Trimethylsilyldiazomethane → Methyl 4-hydroxy-1-methylpyrrolidine-2-carboxylate

HRID 1785988Notes

Reaction equation

HRID 1785988 reaction equation
[OH:1][CH:2]1[CH2:6][N:5]([CH3:7])[CH:4]([C:8]([OH:10])=[O:9])[CH2:3]1.[CH3:11][Si](C=[N+]=[N-])(C)C>CO>[CH3:11][O:9][C:8]([CH:4]1[CH2:3][CH:2]([OH:1])[CH2:6][N:5]1[CH3:7])=[O:10]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 2370404-Hydroxy-1-methylpyrrolidine-2-carboxylic acid

Product 1

HCID 15594655Methyl 4-hydroxy-1-methylpyrrolidine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Hydroxy-1-methyl-pyrrolidine-2-carboxylic acid (0.27 g, 1.85 mmol) was dissolved in 5 ml methanol at room temperature and (trimethylsilyl)diazomethane (2M solution in hexane) was added until solution become yellow. The mixture was concentrated down to afford crude 4-hydroxy-1-methyl-pyrrolidine-2-carboxylic acid methyl ester, which was converted to 4-(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)-1-methylpyrrolidine-2-carboxylic acid following the same procedure as for the preparation of (1R,2R)-2-[(4-{[(2S,4R)-4-[acetyl(4-chlorophenyl)amino]-2-methyl-3,4-dihydroquinolin-1(2H)-yl]carbonyl}phenoxy)methyl]cyclopentanecarboxylic acid.

Workup

  1. concentrationThe mixture was concentrated down

Sources & evidence

ORD record
ord-6194b864aa8a4b1e9ac5f444369a9624
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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