(R)-3-(Benzyloxycarbonylamino)-N-hydroxy-pyrrolidine → (R)-3-N-Cbz-aminopyrrolidine

HRID 985716Notes

Reaction equation

HRID 985716 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[CH2:16][CH2:15][N:14](O)[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[Ni]>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[CH2:16][CH2:15][NH:14][CH2:13]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 11651598(R)-3-(Benzyloxycarbonylamino)-N-hydroxy-pyrrolidine

Product 1

HCID 40425229(R)-3-N-Cbz-aminopyrrolidineYield 81%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

The crude (R)-3-(benzyloxycarbonylamino)-N-hydroxy-pyrrolidine obtained above (1.4 g) was dissolved in ethanol (10 ml). Raney nickel (about 2 g) was added to this mixture. The reaction was degassed under reduced pressure and hydrogen supply (three times) and subsequently put under hydrogen atmosphere (1 bar). The reaction was over after 6 hours, yielding crude (R)-3-(benzyloxycarbonylamino)-pyrrolidine which was further processed in situ, in that di-tert-butyl dicarbonate (1.0 g, 4.58 mmol) was added; the mixture was stirred for one hour. The solvent was removed and the residue taken up in an n-hexane/AcOEt mixture (1:1, 20 ml) and filtered through a silicagel pad. The silica was washed with n-hexane/AcOEt mixture (1:1; 250 ml). The organic phases were evaporated. The compound was obtained as a colorless oil (1.125 g; yield 81%) in good purity, i.e. at least 90-95%, rendering the compound sufficiently pure for further reaction, e.g. in Example 3.

Workup

  1. customThe reaction was degassed under reduced pressure and hydrogen supply (three times)
  2. customafter 6 hours

Sources & evidence

ORD record
ord-75bcf1f1115f4042b2d67603311574cd
Source dataset
uspto-grants-2005_03
Patent number
US06872836B2

Reaction notes

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