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 263792Notes

Reaction equation

HRID 263792 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 for 2 h at RT under normal pressure in the presence of 0.5 g of Nishimura catalyst. The catalyst is removed by filtration and the filtrate is then concentrated in a rotary evaporator and dried under a high vacuum. TLC Rf (D)=0.5; FAB-MS (M+H+)=312.

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate is then concentrated in a rotary evaporator
  3. customdried under a high vacuum

Sources & evidence

ORD record
ord-5606e99c4965448698fab25a653045ea
Source dataset
uspto-grants-1997_07
Patent number
US05643878

Reaction notes

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