tert-butyl(1S)-1-[(2S)-5-oxotetrahydrofuran-2-yl]-2-phenylethylcarbamate → (5S)-5-[(1S)-1-(N-t-butoxycarbonylamino)-2-cyclohexylethyl]dihydrofuran-2(3H)-one

HRID 1376663Notes

Reaction equation

HRID 1376663 reaction equation
[C:1]([NH:8][C@H:9]([C@H:17]1[O:21][C:20](=[O:22])[CH2:19][CH2:18]1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>CO>[C:1]([NH:8][C@H:9]([C@H:17]1[O:21][C:20](=[O:22])[CH2:19][CH2:18]1)[CH2:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

3

Reactant 1

HCID 10870461tert-butyl(1S)-1-[(2S)-5-oxotetrahydrofuran-2-yl]-2-phenylethylcarbamate

Product 1

HCID 10946873(5S)-5-[(1S)-1-(N-t-butoxycarbonylamino)-2-cyclohexylethyl]dihydrofuran-2(3H)-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5 g (16.37 mmol) of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-dihydrofuran-2-(3H)-one in 50 ml of methanol is hydrogenated in the presence of 0.5 g of Nishimura catalyst under normal pressure for 2 hours at room temperature. Removal of the catalyst by filtration is followed by concentration in a rotary evaporator and drying under a high vacuum. TLC Rf (D)=0.5; FAB-MS (M+H+)=312.

Workup

  1. customRemoval of the catalyst
  2. filtrationby filtration
  3. concentrationis followed by concentration in a rotary evaporator
  4. customdrying under a high vacuum

Sources & evidence

ORD record
ord-3d3afa2023a94ab9b47475929d29f335
Source dataset
uspto-grants-1997_09
Patent number
US05663168

Reaction notes

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