tert-Butyl (S)-((4-benzylmorpholin-2-yl)methyl)carbamate → (R)-2-N-Boc-aminomethylmorpholine

HRID 15182Notes

Reaction equation

HRID 15182 reaction equation
C1(C[N:8]2[CH2:13][CH2:12][O:11][C@@H:10]([CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:9]2)C=CC=CC=1>C(O)C.[Pd]>[NH:8]1[CH2:13][CH2:12][O:11][C@@H:10]([CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21])[CH2:9]1

Participants

4

Reactant 1

HCID 57691594tert-Butyl (S)-((4-benzylmorpholin-2-yl)methyl)carbamate

Product 1

HCID 42556135(R)-2-N-Boc-aminomethylmorpholineYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1,1-dimethylethyl {[(2S)-4-(phenylmethyl)-2-morpholinyl]methyl}carbamate (4.9 g, 16 mmol) in ethanol (160 mL) was added 10% Pd/C (1.5 μg). The suspension was hydrogenated at 50 psi for 8 h. The reaction was filtered through a pad of Celite® and the pad was washed several times with methanol. The filtrate was concentrated to afford the title compound (3.35 g, 97%) as a colorless solid which was not purified further: LC/MS (ES) m/e 217 (M+H)+. The absolute stereochemistry of the title compound was determined by vibrational circular dichroism (VCD).

Workup

  1. filtrationThe reaction was filtered through a pad of Celite®
  2. washthe pad was washed several times with methanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-5a966029b89b411d84e4a72a082a62ab
Source dataset
uspto-grants-2010_06
Patent number
US07732460B2

Reaction notes

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