Reaction #1747888

Reaction equation

azide

3-Azido-2-tert-butoxycarbonylamino-1-(tert-butyldimethyl-silanyloxy)butane

→

amine

Yield 91.0%

3-Amino-2-tert-Butoxycarbonylamino-1-(tert-butyldimethyl-silanyloxy)butane

Yield 91.0%

Solvents

EtOH

Conditions

Workup

1. 1
   OtherThe reaction was purged with H2
2. 2
   FiltrationThe mixture was filtered through Celite®
3. 3
   ConcentrationThe filtrate was concentrated

Procedure

To a solution of azide 109 (35 mg, 0.10 mmol) in EtOH (1 mL), under argon, 10% Pd/c (7 mg) was added. The reaction was purged with H2 and stirred overnight under H2 atmosphere (1 atm). The mixture was filtered through Celite®. The filtrate was concentrated to yield the amine 110 (29 mg, 90%). The crude residue was used without further purification in the next step. 1H-NMR (500 MHz, CDCl3): 0.05 (s, 6H), 0.90 (s, 9H), 1.12 (d, J=6.7 Hz, 3H), 1.47 (s, 9H), 3.21-3.31 (m, 1H), 3.42-3.48 (m, 1H), 3.63-3.82 (m, 2H), 5.01-5.10 (m, 1H). 13C-NMR (125 MHz, CDCl3): −5.1, 19.1, 21.3, 26.2, 28.8, 47.1, 56.9, 64.5, 176.5.

Source