tert-Butyl 6a-phenyl-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5-carboxylate → tert-Butyl 3-amino-4-(hydroxymethyl)-3-phenyl-pyrrolidine-1-carboxylate

HRID 338097Notes

Reaction equation

HRID 338097 reaction equation
[C:1]1([C:7]23[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12][CH:11]2[CH2:10][O:9][NH:8]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.[Ni]>[NH2:8][C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:11]([CH2:10][OH:9])[CH2:12][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:19])[CH3:20])=[O:16])[CH2:14]1

Participants

4

Reactant 1

HCID 86697908tert-Butyl 6a-phenyl-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5-carboxylate

Product 1

HCID 86697911tert-Butyl 3-amino-4-(hydroxymethyl)-3-phenyl-pyrrolidine-1-carboxylateYield 117%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

tert-Butyl 6a-phenyl-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5-carboxylate (142 mg, 489.04 mmol) is dissolved in methanol (10 mL). The solution is put through a flow hydrogenator with the Raney/Ni catalyst bed at 1 atmosphere H2 pressure and at 20° C., with a flow rate of 1 mL/min. Wash the bed with 10 mL more of MeOH after all the original solution has passed through. Remove the solvent under reduced pressure to obtain the title compound as a clear oil (168 mg, 117%) EI/MS (m/e): 293.3 (M+H).

Workup

  1. washWash the bed with 10 mL more of MeOH after all the original solution
  2. customRemove the solvent under reduced pressure

Sources & evidence

ORD record
ord-bc9327dd18b5407ea4f6e8e40651cc15
Source dataset
uspto-grants-2014_11
Patent number
US08889856B2

Reaction notes

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