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

HRID 2387235ノート

反応式

HRID 2387235 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-044e2176396f437eac3ae3576bd0267e
出典データセット
uspto-grants-2012_09
特許番号
US08268827B2

反応ノート

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