Trimethylsilyldiazomethane → 1-tert-Butyl 2-methyl (2S)-2-methylpyrrolidine-1,2-dicarboxylate

HRID 1961401Notes

Reaction equation

HRID 1961401 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@:9]1([CH3:16])[C:13]([OH:15])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Si](C=[N+]=[N-])(C)(C)[CH3:18]>CO.CCOCC>[CH3:16][C@@:9]1([C:13]([O:15][CH3:18])=[O:14])[CH2:10][CH2:11][CH2:12][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 11206950(2S)-1-(tert-Butoxycarbonyl)-2-methylpyrrolidine-2-carboxylic acid

Product 1

HCID 594364261-tert-Butyl 2-methyl (2S)-2-methylpyrrolidine-1,2-dicarboxylateYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of (S)-1-(tert-butoxycarbonyl)-2-methylpyrrolidine-2-carboxylic acid 106A in methanol (100 ml) and ether (100 ml) was added TMS-Diazomethane (80 ml) (2.0 M ether solution) dropwise at 0° C. The reaction mixture was stirred at room temperature for 2 h and the reaction mixture was concentrated. The residue was purified by flash chromatography (10% EtOAc/Hexane) to give (S)-1-tent-butyl 2-methyl 2-methylpyrrolidine-1,2-dicarboxylate 106B (28.5 g, 76% overall yield) as an oil. 1H NMR (CDCl3, 400 MHz) δ 3.69 (s, 3H), 3.42-3.56 (m, 2H), 2.13-2.17 (m, 1H), 1.83-1.93 (m, 3H), 1.49 (s, 3H), 1.39 (s, 9H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customThe residue was purified by flash chromatography (10% EtOAc/Hexane)

Sources & evidence

ORD record
ord-3dc453e40ab74c3fb75c9b6c250c6296
Source dataset
uspto-grants-2013_04
Patent number
US08415340B2

Reaction notes

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