Acetic acid methanol → HCID 178476567, 화합물

HRID 2271531노트

반응식

HRID 2271531 반응식
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([NH:11]C(=O)OCC2C=CC=CC=2)[CH2:7][CH2:6]1)[CH3:3].CO.[C:24]([OH:27])(=[O:26])[CH3:25]>[Pd]>[C:24]([OH:27])(=[O:26])[CH3:25].[C:24]([OH:27])(=[O:26])[CH3:25].[CH3:3][N:2]([CH2:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([NH2:11])[CH2:7][CH2:6]1)[CH3:1]

참가 물질

4

반응물 2

HCID 10129899Acetic acid methanol2회HCID 66715796Carbamic acid, N-[trans-4-[(dimethylamino)methyl]cyclohexyl]-, phenylmethyl ester

생성물 1

HCID 178476567HCID 178476567, 화합물

시약·촉매·용매 1

HCID 23938Palladium촉매

실험 절차

To a flask containing Pd/C (1.5 g, Degussa type E101) was added methanol/acetic acid (100 mL, 3:1). Benzyl 4-((dimethylamino)methyl)cyclohexylcarbamate (15.8 g, 54 mmol) in methanol/acetic acid (300 mL, 3:1) was added. A balloon of H2 was added and the reaction stirred at rt for 6 h. The reaction was filtered through celite, the filtrate concentrated, and azeotroped with toluene. The thick oil was dried under vacuum to give desired product (17.9 g, crude) as a waxy solid. 1H NMR (300 MHz, MeOD) δ 3.11-2.98 (m, 1H), 2.78 (d, J=7.0 Hz, 2H), 2.69 (s, 6H), 2.07 (br d, J=13.9 Hz, 4H), 2.02-1.86 (m, 2H), 1.92 (s, 6H), 1.79-1.67 (m, 1H), 1.53-1.35 (m, 2H), 1.20-1.05 (m, 2H).

후처리

  1. additionA balloon of H2 was added
  2. filtrationThe reaction was filtered through celite
  3. concentrationthe filtrate concentrated
  4. customazeotroped with toluene
  5. customThe thick oil was dried under vacuum

출처 및 근거

ORD 기록
ord-da74a59c1e6d4ab8b0fba14c9ca384b4
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120749B2

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