(R)-tert-Butyl 1-azido-3-methoxypropan-2-ylcarbamate → tert-butyl N-((2R)-1-amino-3-methoxypropan-2-yl)carbamate

HRID 516080Notes

Reaction equation

HRID 516080 reaction equation
[N:1]([CH2:4][C@@H:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:6][O:7][CH3:8])=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][C@@H:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:14])([CH3:13])[CH3:15])[CH2:6][O:7][CH3:8]

Participants

4

Reactant 1

HCID 86654731(R)-tert-Butyl 1-azido-3-methoxypropan-2-ylcarbamate

Product 1

HCID 59199768tert-butyl N-((2R)-1-amino-3-methoxypropan-2-yl)carbamateYield 19.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (R)-tert-butyl 1-azido-3-methoxypropan-2-ylcarbamate (4.3 g, 18.7 mmol) and 10% Pd/C (1.5 g) in MeOH was stirred at RT under H2 atmosphere overnight. After filtration, the crude product was purified by amino-protected silica gel chromatography eluting with EtOAc and petroleum ether (EtOAc/PE=1/1) to give the title compound (740 mg, 19.4%). 1H NMR (400 MHz, CD3OD) δ ppm 5.00 (s, 1 H), 3.67-3.66 (m, 1 H), 3.51-3.47 (m, 1H), 3.42-3.38 (m, 1 H), 3.35 (s, 1 H), 2.82-2.78 (m, 2 H), 1.46 (s, 9 H). [M+H] calc'd for C9H20N2O3, 205; found, 205.

Workup

  1. filtrationAfter filtration
  2. customthe crude product was purified by amino-protected silica gel chromatography
  3. washeluting with EtOAc and petroleum ether (EtOAc/PE=1/1)

Sources & evidence

ORD record
ord-bb7f5c19a02b45bcb5dc43dedf88183d
Source dataset
uspto-grants-2015_08
Patent number
US09108970B2

Reaction notes

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