benzyl (S)-1-((1S,2S,4R)-4-(tert-butyldimethylsilyloxy)-2-isopropylcyclohexyl)-2-oxopyrrolidin-3-ylcarbamate → benzyl (S)-1-((1S,2S,4R)-4-hydroxy-2-isopropylcyclohexyl)-2-oxopyrrolidin-3-ylcarbamate

HRID 1374304Notes

Reaction equation

HRID 1374304 reaction equation
[Si]([O:8][C@@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[CH2:19][CH2:18][C@H:17]([NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:16]2=[O:31])[C@H:11]([CH:32]([CH3:34])[CH3:33])[CH2:10]1)(C(C)(C)C)(C)C>CC(O)=O.C1COCC1.O>[OH:8][C@@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[CH2:19][CH2:18][C@H:17]([NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:16]2=[O:31])[C@H:11]([CH:32]([CH3:34])[CH3:33])[CH2:10]1

Participants

3

Reactant 1

HCID 86596870benzyl (S)-1-((1S,2S,4R)-4-(tert-butyldimethylsilyloxy)-2-isopropylcyclohexyl)-2-oxopyrrolidin-3-ylcarbamate

Product 1

HCID 86596869benzyl (S)-1-((1S,2S,4R)-4-hydroxy-2-isopropylcyclohexyl)-2-oxopyrrolidin-3-ylcarbamateYield 97.9%

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent2×

Procedure

Benzyl (S)-1-((1S,2S,4R)-4-(tert-butyldimethylsilyloxy)-2-isopropylcyclohexyl)-2-oxopyrrolidin-3-ylcarbamate (1.0 g) was dissolved in a 4/1/1 mixture of AcOH/THF/H2O (60 mL). After 72 h, additional 4/1/1 mixture of AcOH/THF/H2O (30 mL) was added. This solution was stirred an additional 24 h before it was concentrated. The residue was dissolved in EtOAc and washed with saturated NaHCO3, dried (MgSO4), filtered, and concentrated in vacuo to afford benzyl (S)-1-((1S,2S,4R)-4-hydroxy-2-isopropylcyclohexyl)-2-oxopyrrolidin-3-ylcarbamate (750 mg). MS found: (M+H)+=375.3.

Workup

  1. additionwas added
  2. concentrationwas concentrated
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with saturated NaHCO3
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-53b20c646a5a46158b2bee974ff27d78
Source dataset
uspto-grants-2007_01
Patent number
US07163937B2

Reaction notes

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