Trifluoroacetic acid → Carbamic acid, N-[3-(cyclohexylamino)propyl]-, 1,1-dimethylethyl ester

HRID 2387235노트

반응식

HRID 2387235 반응식
[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]

참가 물질

6

반응물 3

HCID 6422Trifluoroacetic acidHCID 7967CyclohexanoneHCID 2735700tert-Butyl (3-aminopropyl)carbamate

생성물 1

HCID 79032436Carbamic acid, N-[3-(cyclohexylamino)propyl]-, 1,1-dimethylethyl ester수율 46%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

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)+.

후처리

  1. washwashed sequentially with sat. aq. NaHCO3 solution and brine
  2. dry with materialThe solution was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel
  6. washeluting with EtOAc

출처 및 근거

ORD 기록
ord-044e2176396f437eac3ae3576bd0267e
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268827B2

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