(2R,3R)-2-(3-chlorophenyl)-3,5,5-trimethyl-2-morpholinol → Bupropion Morpholinol (2R,3R)-Isomer

HRID 890588

반응식

HRID 890588 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C@@:8]2([OH:17])[O:13][CH2:12][C:11]([CH3:15])([CH3:14])[NH:10][C@@H:9]2[CH3:16])[CH:5]=[CH:6][CH:7]=1>C(OCC)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C@@:8]2([OH:17])[O:13][CH2:12][C:11]([CH3:14])([CH3:15])[NH:10][C@@H:9]2[CH3:16])[CH:5]=[CH:6][CH:7]=1

참가 물질

3

반응물 1

HCID 9943908(2R,3R)-2-(3-chlorophenyl)-3,5,5-trimethyl-2-morpholinol

생성물 1

HCID 9943907Bupropion Morpholinol (2R,3R)-Isomer수율 90%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

Hydrochloride salts of the separated enantiomers were obtained by the following processes. 1.25 g (0.005 mol) of optical isomer 1 (retention time 6.117 min) ((−)-(2R,3R)-2-(3-chlorophenyl)-3,5,5-trimethyl-2-morpholinol) was dissolved in diethyl ether. The solution was filtered and the filtrate was chilled in an ice-bath adding ethereal hydrogen chloride until the solution was acidic. After standing at ambient temperature for 24 h, the resulting solid was filtered, washed with diethyl ether and dried in a vacuum oven at 60° C. for 18 h to give 1.32 g (90%) of (−)-(2R,3R)-2-(3-chlorophenyl)-3,5,5-trimethyl-2-morpholinol hydrochloride as a white solid: mp 208–209° C. NMR (300 Mhz, DMSO-d6); δ 9.72 (br, 1H), 8.76 (br, 1H), 7.54–7.41 (m, 5H), 3.98 (d, 1H), 3.52 (d, 1H), 3.37 (br s, 1H), 1.53 (s, 3H), 1.29 (s, 3H), 0.97 (d, 3H). Anal. Calcd for C13H19Cl2NO2: C, 53.43; H, 6.55; N, 4.79. Found: C, 53.35; H, 6.57; N, 4.71. [α]D20° C.=−33.2° (0.67, 95% EtOH)

후처리

  1. filtrationThe solution was filtered
  2. temperaturethe filtrate was chilled in an ice-bath
  3. additionadding ethereal hydrogen chloride until the solution
  4. filtrationthe resulting solid was filtered
  5. washwashed with diethyl ether
  6. customdried in a vacuum oven at 60° C. for 18 h

출처 및 근거

ORD 기록
ord-8bf11dc0be5b41829bb712fbd29ad4a4
출처 데이터셋
uspto-grants-2006_02
특허 번호
US06998400B2

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