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

HRID 2246598Notes

Reaction equation

HRID 2246598 reaction equation
C(OC([NH:11][C@H:12]1[CH2:16][CH2:15][N:14]([C@H:17]2[CH2:22][CH2:21][C@@H:20]([NH:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:19][C@H:18]2[NH:28][C:29](=[O:37])[O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:13]1=[O:38])=O)C1C=CC=CC=1.[H][H]>CO.[Pd]>[NH2:11][C@H:12]1[CH2:16][CH2:15][N:14]([C@H:17]2[CH2:22][CH2:21][C@@H:20]([NH:23][C:24]([CH3:26])([CH3:27])[CH3:25])[CH2:19][C@H:18]2[NH:28][C:29](=[O:37])[O:30][CH2:31][CH2:32][Si:33]([CH3:34])([CH3:36])[CH3:35])[C:13]1=[O:38]

Participants

5

Reactant 2

HCID 866181402-(trimethylsilyl)ethyl (1R,2S,5R)-2-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-5-(tert-butylamino)cyclohexylcarbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 866181602-(trimethylsilyl)ethyl (1R,2S,5R)-2-((S)-3-amino-2-oxopyrrolidin-1-yl)-5-(tert-butylamino)cyclohexylcarbamateYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  1. filtrationthe solution was filtered
  2. concentrationconcentrated in vacuo
  3. waitAfter 1 h
  4. filtrationthe solution was filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7978d2fc512443668a899ad9e3ea911c
Source dataset
uspto-grants-2010_03
Patent number
US07687508B2

Reaction notes

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