Trifluoroacetic acid → Carbamic acid, N-[3-(cyclohexylamino)propyl]-, 1,1-dimethylethyl ester
Reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].C(O)(C(F)(F)F)=O>CO.CCOC(C)=O>[C:15]([O:14][C:13](=[O:19])[NH:12][CH2:11][CH2:10][CH2:9][NH:8][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)([CH3:18])([CH3:16])[CH3:17]Participants
Procedure
A solution of cyclohexanone (6.0 eq) and tert-butyl (3-aminopropyl)carbamate (1.0 eq) in MeOH (1.5 M) was stirred at RT for 2 h and treated with NaBH3(CN) (6.0 eq). TFA was added until pH 6, and stirring was continued for 24 h at RT. The reaction mixture was diluted with EtOAc, washed sequentially with sat. aq. NaHCO3 solution and brine. The solution was dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with EtOAc to afford the title compound EE1 (46% yield). 1H-NMR (500 MHz, DMSO-d6, 300K) δ: 8.12 (1H, br. s), 3.04-2.91 (3H, m), 2.91-2.82 (2H, m), 2.00-1.91 (1H, m), 1.78-1.53 (5H, m), 1.37 (9H, s), 1.24-1.12 (6H, m). MS (ES) C14H28N2O2 required: 256, found: 257 (M+H)+.
Workup
- washwashed sequentially with sat. aq. NaHCO3 solution and brine
- dry with materialThe solution was dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe crude product was purified by column chromatography on silica gel
- washeluting with EtOAc
Sources & evidence
- ORD record
- ord-044e2176396f437eac3ae3576bd0267e
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08268827B2
Reaction notes
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