Ethyl Acetate → Benzyl 3-amino-4-(hydroxymethyl)-3-phenyl-pyrrolidine-1-carboxylate

HRID 338098Notes

Reaction equation

HRID 338098 reaction equation
[C:1]1([C:7]23[CH2:14][N:13]([C:15]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[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.C(OCC)(=O)C>C(O)(=O)C.[Zn]>[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][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16])[CH2:14]1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 86697899Benzyl 6a-phenyl-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5-carboxylate

Product 1

HCID 86697912Benzyl 3-amino-4-(hydroxymethyl)-3-phenyl-pyrrolidine-1-carboxylateYield 99%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Powdered zinc (43.7 g, 669 mmol) is added to a solution of benzyl 6a-phenyl-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5-carboxylate (31 g, 96 mmol) in acetic acid (310 mL) and the mixture is stirred for 30 minutes. Ethyl acetate (500 mL) is added and the mixture is filtered through diatomaceous earth. The solvent is removed under vacuum and the crude product is re-dissolved in ethyl acetate. Water is added to the solution and the pH is adjusted to 10 with 2 M NaOH. The solution is filtered through diatomaceous earth, the layers are separated, and the organic layer is dried over magnesium sulfate, and concentrated to give the title compound (31 g, 99%). ES/MS (m/e): 327 (M+H).

Workup

  1. filtrationthe mixture is filtered through diatomaceous earth
  2. customThe solvent is removed under vacuum
  3. dissolutionthe crude product is re-dissolved in ethyl acetate
  4. additionWater is added to the solution
  5. filtrationThe solution is filtered through diatomaceous earth
  6. customthe layers are separated
  7. dry with materialthe organic layer is dried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c86a91c2a13e44cdb280750b7b8e6afb
Source dataset
uspto-grants-2014_11
Patent number
US08889856B2

Reaction notes

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