Ammonium formate → 4-Amino-4-methyl-cyclohexanol

HRID 1293384노트

반응식

HRID 1293384 반응식
C(OC(=O)[NH:10][C:11]1([CH3:18])[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)(C)C>[NH2:10][C:11]1([CH3:18])[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1

참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 66756996benzyl N-(4-hydroxy-1-methylcyclohexyl)carbamate

생성물 1

HCID 223798474-Amino-4-methyl-cyclohexanol

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 3776Isopropanol용매

실험 절차

A mixture of example 45E (169 mg, 0.64 mmol), ammonium formate (105 mg, 1.67 mmol) and 10% palladium on carbon (7 mg) in isopropanol (5 mL) was heated at 80° C. for 1 hour. The reaction mixture was cooled and filtered through a plug of Celite. The filter pad was washed with ethyl acetate (50 mL), and the filtrate was concentrated in vacuo to afford the titled compound as an inseparable mixture of diastereomers. MS (CI) m/z 130 (M+1)+; 1H NMR (300 MHz, CDCl3) δ ppm 3.77-3.71 (m, 2H), 3.65-3.61 (m, 2H), 1.87-1.61 (m, 4H), 1.63-1.33 (m, 10H), 1.15 (s, 3H), 1.11 (s, 3H).

후처리

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered through a plug of Celite
  3. washThe filter pad was washed with ethyl acetate (50 mL)
  4. concentrationthe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-bb9c650cc17a40319fcf6493643c4a50
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07238724B2

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