Trimethylsilyldiazomethane → 1-Tert-butyl 3-methyl 3-aminopyrrolidine-1,3-dicarboxylate

HRID 1038094Notes

Reaction equation

HRID 1038094 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[NH2:8][C:9]1([C:21]([O-:23])=[O:22])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]1>CO>[CH3:1][O:22][C:21]([C:9]1([NH2:8])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:10]1)=[O:23]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 860631201,3-Pyrrolidinedicarboxylic acid, 3-amino-, 1-(1,1-dimethylethyl) ester

Product 1

HCID 576862811-Tert-butyl 3-methyl 3-aminopyrrolidine-1,3-dicarboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Added (Trimethylsilyl)-diazomethane (2M in hexanes: 15 ml, 30 mmol) to a solution of 3-Amino pyrrolidine 1,3 dicarboxylic acid, 1-tert-butyl ester (900 mg, 3.9 mmol) in MeOH (5 ml) at room temperature. Stirred 10 minutes then evaporated solvent yielding 1T as an oil (0.9 g, 98%).

Sources & evidence

ORD record
ord-1fae8528d0ae4ed298eef3996e62bbe2
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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