87691-27-8

Basic information

• Product Name: N-Boc-cis-4-Hydroxy-L-proline
• Synonyms: (2S,4S)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester;(2S,4S)-cis-1-N-Boc-4-hydroxy-proline, N- Boc-cis-4-hydroxypyrrolidine-2-carboxylic acid;cis-boc-Hyp-OH;cis-N-Boc-4-hydroxy-L-proline;cis-1-(tert-Butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid;cis-N-Boc-4-hydroxy-L-proline, 97+%;1,2-Pyrrolidinedicarboxylic acid, 4-hydroxy-, 1-(1,1-dimethylethyl) ester, (2S,4S)-;N-Boc-cis-4-hydroxy-L-proline 97%
• CAS NO: 87691-27-8
• Molecular Formula: C₁₀H₁₇NO₅
• Molecular Weight: 231.25
• EINECS: 1312995-182-4
• Product Categories: Carboxylic Acids;Carboxylic Acids;Pyrrolidines
• Mol File: 87691-27-8.mol
• Article Data: 37

Chemical Properties

• Melting Point: 146 °C (D)(lit.)
• Boiling Point: 390.9oC at 760 mmHg
• Flash Point: 190.2oC
• Appearance: White to off-white/Powder or Crystalline Powder
• Density: 1.312 g/cm³
• Vapor Pressure: 9.99E-08mmHg at 25°C
• Refractive Index: 1.531
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 3.80±0.40(Predicted)
• CAS DataBase Reference: N-Boc-cis-4-Hydroxy-L-proline(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-cis-4-Hydroxy-L-proline(87691-27-8)
• EPA Substance Registry System: N-Boc-cis-4-Hydroxy-L-proline(87691-27-8)

Safety Data

• Hazard Codes: Xi,N
• Statements: 36/37/38-50
• Safety Statements: 26-36/37-60-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 87691-27-8(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C10H17NO5/c1-10(2,3)16-9(15)11-5-6(12)4-7(11)8(13)14/h6-7,12H,4-5H2,1-3H3,(H,13,14)/t6-,7-/m0/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 618-27-9 hydroxy L-proline 
• 84348-37-8 N-tert-butoxycarbonyl-4-oxo-L-proline 
• 147-85-3 L-proline 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 
• 168264-25-3 Boc-(2S,4S)-p-nitrobenzoate-4-hydroxyproline methyl ester 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 1332341-02-2 benzyl (2S)-2-Boc-amino-3-(2-oxiranyl)propionate 
• 51-35-4 4R-4-hydroxyproline 
• 87250-97-3 tert-butyl 3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate 
• 87250-97-3 2’-methyl-2’-propanyl (1S,4S)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate 
• 74844-91-0 (2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester 
• 502442-58-2 ethyl (4S)-2-(N-tert-butyloxycarbonylamino)-5-tert-butyldimethylsiloxy-4-tert-butyldiphenylsiloxy-2-pentenoate 
• 502442-60-6 ethyl (4S)-2-(N-tert-butyloxycarbonylamino)-4-tert-butyldiphenylsiloxy-5-hydroxy-2-pentenoate 

Downstream Products

• 266337-25-1 (4S)-1-(tert-butoxycarbonyl)-4-hydroxy-L-prolinamide 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 96314-28-2 (2S,4R)-1-(tert-butoxycarbonyl)-4-(tosyloxy)pyrrolidine-2-carboxylic acid 
• 51-35-4 4R-4-hydroxyproline 
• 74844-91-0 (2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester 
• 958879-76-0 N-tert-butyloxycarbonyl-(2S,4R)-4-thioacetyl-proline benzyl ester 
• 958879-77-1 N-tert-butyloxycarbonyl-(2S,4R)-4-thioproline 
• 176306-18-6 [R-(R*,S*)]-4-[(Triphenylmethyl)thio]-1,2-pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester 
• 132622-91-4 (4S)-1-(tert-butoxycarbonyl)-4-<(methylsulfonyl)oxy>-L-proline benzyl ester 
• 40350-83-2 (2S,4S)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid 
• 143035-54-5 C₆H₁₂N₂O₂ 
• 132622-94-7 (4R)-1-(tert-butoxycarbonyl)-4-cyano-L-proline benzyl ester 
• 152892-83-6 (2S,4S)-2-benzyl 1-tert-butyl 4-(benzyloxy)pyrrolidine-1,2-dicarboxylate 

Relevant articles and documents

Automated Radiosynthesis of cis- And trans-4-[18F]Fluoro- l -proline Using [18F]Fluoride

The positron emission tomography imaging agents cis- and trans-4-[18F]fluoro-l-proline are used for the detection of numerous diseases such as pulmonary fibrosis and various carcinomas. These imaging agents are typically prepared by nucleophilic fluorination of 4-hydroxy-l-proline derivatives, with [18F]fluoride, followed by deprotection. Although effective radiofluorination reactions have been developed, the overall radiosynthesis process is suboptimal due to deprotection methods that are performed manually, require multiple steps, or involve harsh conditions. Here we describe the development of two synthetic routes that allow access to precursors, which undergo highly selective radiofluorination reactions and rapid deprotection, under mild acidic conditions. These methods were found to be compatible with automation, avoiding manual handling of radioactive intermediates.

Orthogonal Catalysis for an Enantioselective Domino Inverse-Electron Demand Diels?Alder/Substitution Reaction

An enantioselective domino process for the synthesis of substituted 1,2-dihydronaphthalenes has been developed by the combination of chiral amines and a bidentate Lewis acid in an orthogonal catalysis. This new method is based on an inverse electron-demand Diels?Alder and a subsequent group exchange reaction. An enamine is generated in situ from an aldehyde and a chiral secondary amine catalyst that reacts with phthalazine, activated by the coordination to a bidentate Lewis acid catalyst. The absolute configuration of the product is controlled by chiral information provided by the amine. The formed ortho-quinodimethane intermediate is then transformed via a group exchange reaction with thiols. The new method shows a broad scope and tolerates a wide range of functional groups with enantiomeric ratios up to 91 : 9. All-in-all, this enantioselective synthesis tool provides an easy access to complex 1,2-dihydronaphthalenes starting from readily available phthalazine, aldehydes and thiols in a combinatorial way.

Pyrrolidine ring puckering and prolyl amide bond configurations of 2-methyl-allo-hydroxyproline-based dipeptides

An expeditious method for the synthesis of homo and heterochiral dipeptides containing l-alanine and d/l 2-methyl allo-hydroxyl prolines was developed using direct aminolysis of bicyclic lactones derived from d/l alanine. The impact of C-2 methylation and its spatial orientation on the pyrrolidine ring puckering and prolyl amide bond configuration was ascertained by solution NMR studies. The present studies reveal that C-2 methylation causes the prolyl amide bond to exist exclusively in the trans geometry in both homo- and heterochiral dipeptides. However, the spatial orientation of the C-2 methyl group and its i + 2 position in appropriately capped model dipeptides may nucleate into a turn like structure.