3-(((benzyloxy)carbonyl)amino)-N-(2-butoxyethyl)-N,N,3-trimethylbutan-1-aminium chloride → 3-amino-N-(2-butoxyethyl)-N,N,3-trimethylbutan-1-aminium chloride
Reaction equation
[Cl-:1].C(OC([NH:12][C:13]([CH3:27])([CH3:26])[CH2:14][CH2:15][N+:16]([CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH3:25])([CH3:18])[CH3:17])=O)C1C=CC=CC=1>CO>[Cl-:1].[NH2:12][C:13]([CH3:26])([CH3:27])[CH2:14][CH2:15][N+:16]([CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH3:25])([CH3:18])[CH3:17]Participants
Procedure
Under a nitrogen atmosphere, 10% pd/C (100 mg) was added to a solution of 3-(((benzyloxy)carbonyl)amino)-N-(2-butoxyethyl)-N,N,3-trimethylbutan-1-aminium chloride (0.38 g, 0.95 mmol) in 4 mL of methanol. The flask was degassed and placed under a hydrogen atmosphere, stirring for 24 hours at room temperature. The suspension was filtered through a pad of celite washing with methanol, and the filtrate was concentrated under reduced pressure to give 252 mg of clear viscous oil (quantitative yield). 1H NMR (400 MHz, D2O) δ 0.78-0.82 (t, J=7.4 Hz, 3H), 1.08 (s, 6H), 1.22-1.30 (sext, J=7.4 Hz, 6H), 1.45-1.52 (m, 2H), 1.77-1.81 (m, 2H), 3.04 (s, 6H), 3.36-3.40 (m, 2H), 3.45-3.49 (t, J=6.5 Hz, 2H), 3.82-3.83 (br m, 2H); LRMS (ESI/APCI) m/z 231 [M]+.
Workup
- customThe flask was degassed
- filtrationThe suspension was filtered through a pad of celite
- washwashing with methanol
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-ba5b7e6be79e4b3fb7633057173b6f6c
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09248117B2
Reaction notes
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