L-Proline, 4-hydroxy-1-methyl-, methyl ester, trans- (9CI)

Base Information

• Chemical Name: L-Proline, 4-hydroxy-1-methyl-, methyl ester, trans- (9CI)
• CAS No.: 13135-69-8
• Molecular Formula: C₇H₁₃NO₃
• Molecular Weight: 159.185
• Hs Code.: 2933998090
• Mol file: 13135-69-8.mol

Synonyms:L-Proline,4-hydroxy-1-methyl-, methyl ester, trans-; Norachilleine, methyl ester (6CI);Proline, 4-hydroxy-1-methyl-, methyl ester, L- (8CI);N-Methyl-trans-4-hydroxy-L-proline methyl ester

Chemical Property of L-Proline, 4-hydroxy-1-methyl-, methyl ester, trans- (9CI)

Chemical Property:

• Melting Point: 53-54 °C
• Boiling Point: 102 °C
• PKA: 14.48±0.40(Predicted)
• PSA: 49.77000
• Density: 1.184±0.06 g/cm3(Predicted)
• LogP: -0.83770
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

98%min ^*data from raw suppliers

(R)-1-Methyl-4-hydroxy-l-prolinemethylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Proline, 4-hydroxy-1-methyl-, methyl ester, trans- (9CI)

There total 6 articles about L-Proline, 4-hydroxy-1-methyl-, methyl ester, trans- (9CI) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (R)-4-hydroxy-L-proline ethyl ester (1499-56-5,775275-31-5,790644-51-8,754962-86-2) → (2S,4R)-methyl 4-hydroxy-1-methylpyrrolidine-2-carboxylate (13135-69-8)

Guidance literature:

With formic acid; water; for 7h; Heating;

DOI:10.1002/(SICI)1521-3773(19980504)37:8<1140::AID-ANIE1140>3.0.CO;2-W

Reference yield:

4R-4-hydroxyproline (51-35-4,30724-02-8) → (2S,4R)-methyl 4-hydroxy-1-methylpyrrolidine-2-carboxylate (13135-69-8)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂ / 6 h / Heating

2: HCO₂H, H₂O / 7 h / Heating

With formic acid; thionyl chloride; water;

DOI:10.1002/(SICI)1521-3773(19980504)37:8<1140::AID-ANIE1140>3.0.CO;2-W

Reference yield:

(2S,4R)-2-methoxycarbonyl-4-hydroxypyrrolidine acetate (114358-11-1) → (2S,4R)-methyl 4-hydroxy-1-methylpyrrolidine-2-carboxylate (13135-69-8)

Guidance literature:

upstream raw materials:

methanol

(2S, 4R)-4-hydroxy-1-methyl-2-pyrrolidinecarboxylic acid

formaldehyd

(R)-4-hydroxy-L-proline ethyl ester

Downstream raw materials:

(E)-3-[(2S,4R)-4-(tert-butyl(dimethyl)silyl)oxy-1-methylpyrrolidin-2-yl]-N-[4-[[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolyl]prop-2-enoylamine

(E)-N-[4-[[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolinyl]-3-[(2S,4R)-4-hydroxy-1-methyl-pyrrolidin-2-yl]propan-2-enoylamine

Refernces

• 1、 -. "6-AMINO QUINAZOLINE OR 3-CYANO QUINOLINE DERIVATIVES, PREPARATION PROCESS AND PHARMACEUTICAL USE THEREOF". Page/Page column 36; 37. . Retrieved 2016/10/08.
• 2、 Sudau, Alexander,Nubbemeyer, Udo. "Unusual diastereoselection in the synthesis of nine-membered ring lactams and conformation-controlled transannular reactions to generate optically active indolizidinones". . p. 1140 - 1143. Retrieved 2007/10/03.