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

HRID 711505Notes

Reaction equation

HRID 711505 reaction equation
[N:1]([CH2:4][C@@H:5]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:6][O:7][CH2:8][CH3:9])=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][C@@H:5]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:6][O:7][CH2:8][CH3:9]

Participants

4

Reactant 1

HCID 86654722(R)-tert-Butyl 1-azido-3-ethoxypropan-2-ylcarbamate

Product 1

HCID 86654723tert-butyl N-((2R)-1-amino-3-ethoxypropan-2-yl)carbamateYield 67.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A mixture of (R)-tert-butyl 1-azido-3-ethoxypropan-2-ylcarbamate (1.2 g, 4.91 mmol) in MeOH (10 mL) was added palladium on carbon (0.523 g, 4.91 mmol). The mixture was stirred under hydrogen atmosphere overnight at RT. The resulting crude material was reconstituted in MeOH (1.0 mL) and purified via reverse phase preparative HPLC. The fractions were collected and solvent was stripped to dryness via rotary evaporation to give the title compound as clear oil (722 mg, 67%). [M+H] calc'd for C10H22N2O3, 219. found, 219.

Workup

  1. custompurified via reverse phase preparative HPLC
  2. customThe fractions were collected
  3. customsolvent was stripped to dryness via rotary evaporation

Sources & evidence

ORD record
ord-c5f1883af25146e4ae8f785bee32a968
Source dataset
uspto-grants-2015_11
Patent number
US09181255B2

Reaction notes

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