(S)-tert-butyl(1-azidobutan-2-yl)carbamate → tert-butyl N-((2S)-1-aminobutan-2-yl)carbamate

HRID 576695Notes

Reaction equation

HRID 576695 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C@@H:8]([CH2:13][CH3:14])[CH2:9][N:10]=[N+]=[N-])([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([O:5][C:6](=[O:15])[NH:7][C@@H:8]([CH2:13][CH3:14])[CH2:9][NH2:10])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 131732866(S)-tert-butyl(1-azidobutan-2-yl)carbamate

Product 1

HCID 45091848tert-butyl N-((2S)-1-aminobutan-2-yl)carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (S)-tert-butyl(1-azidobutan-2-yl)carbamate (7 g, 33 mmol) and 10% Pd/C (777 mg, 0.73 mmol) in EtOAc (150 mL) was stirred under hydrogen (60 psi) for 2 h. The reaction mixture was filtered through Celite and concentrated to give the desired product as a white semi-solid. 1H NMR (400 MHz, DMSO-d6) δ 6.50 (d, J=8.7 Hz, 1H), 3.23-3.12 (m, 1H), 2.45 (d, J=6.0 Hz, 2H), 1.51-1.40 (m, 1H), 1.38 (s, 9H), 1.32-1.20 (m, 3H), 0.80 (t, J=7.4 Hz, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-50066bf3f64844f19766445348e86546
Source dataset
uspto-grants-2015_05
Patent number
US09040534B2

Reaction notes

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