2-(trimethylsilyl)ethyl (1R,2S,5R)-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-(tert-butylamino)cyclohexylcarbamate → 2-(trimethylsilyl)ethyl (1R,2S,5R)-2-((S)-3-amino-2-oxopyrrolidin-1-yl)-5-(tert-butylamino)cyclohexylcarbamate

Participants

Reaction Steps

A sample of 2-(trimethylsilyl)ethyl (1R,2S,5R)-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-(tert-butylamino)cyclohexylcarbamate and its 5S diastereomer (68 mg, 0.141 mmol; see Example 11, Step 4) was dissolved in MeOH (3 mL) prior to the addition of 10% Pd/C (100 mg, 0.940 mmol) and a hydrogen balloon. After 1 h, the solution was filtered and concentrated in vacuo. The reaction was then set-up again with fresh reagents. After 1 h, the solution was filtered and concentrated to give 2-(trimethylsilyl)ethyl (1R,2S,5R)-2-((S)-3-amino-2-oxopyrrolidin-1-yl)-5-(tert-butylamino)cyclohexylcarbamate as a mixture with its 5S diastereomer (139.4 mg, 0.338 mmol, 99% yield): LC/MS found [M+H]+=413.4.

Provenance & Evidence