(S)-4-(benzylamino-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester → (S)-tert-Butyl 4-(aminomethyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 539980Notes

Reaction equation

HRID 539980 reaction equation
C([NH:8][CH2:9][C@H:10]1[CH2:14][O:13][C:12]([CH3:16])([CH3:15])[N:11]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CO>[NH2:8][CH2:9][C@H:10]1[CH2:14][O:13][C:12]([CH3:15])([CH3:16])[N:11]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]

Participants

4

Reactant 1

HCID 68714325(S)-4-(benzylamino-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 71262164(S)-tert-Butyl 4-(aminomethyl)-2,2-dimethyloxazolidine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl (4S)-4-[(benzylamino)methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (810 mg, 2.53 mmol), palladium hydroxide on carbon (81 mg) and methanol (20 mL) was stirred at room temperature under hydrogen atmosphere overnight. The catalyst was removed by filtration. The filtrate was concentrated in vacuo. The residue was purified by SPE (12 mL tube, 2 gram of DSC-SCX) to afford the pure product.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe residue was purified by SPE (12 mL tube, 2 gram of DSC-SCX)
  4. customto afford the pure product

Sources & evidence

ORD record
ord-000634e28b604971906031d7a7104a92
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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