(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 218425Notes

Reaction equation

HRID 218425 reaction equation
[N:1]([CH2:4][C@@H:5]([N:13]([CH3:17])[C:14](=[O:16])[O-:15])[CH2:6][C@H:7]1[CH2:12][CH2:11][CH2:10][O:9][CH2:8]1)=[N+]=[N-]>CCOC(C)=O.[Pd]>[NH2:1][CH2:4][C@@H:5]([N:13]([CH3:17])[C:14](=[O:16])[O:15][C:7]([CH3:12])([CH3:8])[CH3:6])[CH2:6][C@H:7]1[CH2:12][CH2:11][CH2:10][O:9][CH2:8]1

Participants

4

Reactant 1

HCID 86637153(S)-1-azido-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl(methyl)carbamate

Product 1

HCID 58011482tert-Butyl ((S)-1-amino-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl)(methyl)carbamateYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Hydrogenation of (S)-1-azido-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl(methyl)carbamate (62 mg, 0.51 mmol) was carried out in EtOAc (20 mL), 10% Pd/C (15 mg) under 40 psi of H2 for 2 h. After filtration 52 mg of tert-butyl (S)-1-amino-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-ylcarbamate was obtained, yield 91%. MS ESI+ve m/z 273 (M+H).

Workup

  1. filtrationAfter filtration 52 mg of tert-butyl (S)-1-amino-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-ylcarbamate
  2. customwas obtained

Sources & evidence

ORD record
ord-601756a4cf164025adcd73a8662bfce8
Source dataset
uspto-grants-2012_06
Patent number
US08198453B2

Reaction notes

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