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

HRID 855855ノート

反応式

HRID 855855 の反応式
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

参加物

5

反応物 2

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

生成物 1

HCID 223798474-Amino-4-methyl-cyclohexanol

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 3776Isopropanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2bc7c2f79903429da4ba2a95cda9236c
出典データセット
uspto-grants-2007_08
特許番号
US07262207B2

反応ノート

読み込み中…