Tert-butyl (1-(2-methylbutanoyl)piperidin-4-yl)carbamate → 1-(4-Amino-1-piperidinyl)-2-methyl-1-butanone
Reaction equation
[CH3:1][CH:2]([CH2:19][CH3:20])[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([NH:11]C(=O)OC(C)(C)C)[CH2:7][CH2:6]1)=[O:4]>Cl.CO>[NH2:11][CH:8]1[CH2:9][CH2:10][N:5]([C:3](=[O:4])[CH:2]([CH3:1])[CH2:19][CH3:20])[CH2:6][CH2:7]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Protected piperidine 15 (1.2 g, 4.55 mmol) was dissolved in HCl/MeOH (2 M). The reaction mixture was stirred at 50° C. for 2 h. The crude was concentrated under vacuo and was washed with dichloromethane twice. The crude was basified by NaOH solution (6N) to pH 12. The crude was extracted by EtOAc for 6 times. The combined organic layers was evaporated under vacuo yielding final product 16 (724 mg, 3.93 mmol, 86%). H-NMR (DMSO-d6) ∂ 0.78 (q, J=6 Hz, 3H), 0.95 (t, J=5 Hz, 3H), 1.09 (m, 2H), 1.26 (m, 1H), 1.53 (m, 1H), 1.74 (m, 2H), 2.67 (m, 2H), 2.80 (br, 1H), 3.03 (br, 1H), 3.87 (d, J=12 Hz, 1H), 4.23 (br, 1H).
Workup
- concentrationThe crude was concentrated under vacuo
- washwas washed with dichloromethane twice
- extractionThe crude was extracted by EtOAc for 6 times
- customThe combined organic layers was evaporated under vacuo
Sources & evidence
- ORD record
- ord-403e7a6452264e0abb9af5728cf4f6d6
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09034903B2
Reaction notes
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