tert-Butyl ((S)-1-azido-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl)(methyl)carbamate → tert-Butyl ((S)-1-amino-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl)(methyl)carbamate

HRID 218440Notes

Reaction equation

HRID 218440 reaction equation
[N:1]([CH2:4][C@@H:5]([N:13]([CH3:21])[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:6][C@H:7]1[CH2:12][CH2:11][CH2:10][O:9][CH2:8]1)=[N+]=[N-].[H][H]>[Pd].C1COCC1>[NH2:1][CH2:4][C@@H:5]([N:13]([CH3:21])[C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])[CH2:6][C@H:7]1[CH2:12][CH2:11][CH2:10][O:9][CH2:8]1

Participants

5

Reactant 2

HCID 58011481tert-Butyl ((S)-1-azido-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl)(methyl)carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 58011482tert-Butyl ((S)-1-amino-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl)(methyl)carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The tert-butyl (S)-1-azido-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl(methyl)carbamate (2.1 g, 7.04 mmol, 1.0 equiv) and Pd/C (10%, 200 mg) were added to a flask. THF (30 mL) was added and the flask fitted with a gas inlet connected to a balloon of hydrogen gas. The flask was evacuated and back-filled with H2 from the balloon. This was repeated twice and the reaction mixture stirred for 17 h at ambient temperature. Analysis by LC/MS showed complete conversion to the desired amine. The catalyst was removed by filtration through a pad of Celite and the mixture evaporated. This provided 1.82 g (94%) of tert-butyl (S)-1-amino-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl(methyl)carbamate.

Workup

  1. customthe flask fitted with a gas inlet
  2. customThe flask was evacuated
  3. additionback-filled with H2 from the balloon
  4. customThe catalyst was removed by filtration through a pad of Celite
  5. customthe mixture evaporated

Sources & evidence

ORD record
ord-444a697fabb443cfb4cfe22f71ba93e1
Source dataset
uspto-grants-2012_06
Patent number
US08198453B2

Reaction notes

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