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 1377150Notes

Reaction equation

HRID 1377150 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 122.2 g (400 mmol) of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]dihydrofuran-2-(3H)-one [preparation, See Example 2b)] in 1500 ml of methanol is hydrogenated, at RT and under low pressure, in the presence of 4.0 g of Nishimura catalyst [Rh(III)- and Pt(IV)-oxide monohydrate, Degussa]. Filtering off the catalyst, and evaporating the filtrate, results in the title compound: TLC Rf (D)=0.54; FAB-MS (M+H)+ =312.

Workup

  1. filtrationFiltering off the catalyst
  2. customevaporating the filtrate

Sources & evidence

ORD record
ord-7573d48c5f53405d8e5d9eff40ead761
Source dataset
uspto-grants-1997_09
Patent number
US05663200

Reaction notes

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