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

HRID 24276

反応式

HRID 24276 の反応式
[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

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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 ) D 20 ⁢ ° ⁢   ⁢ C . = - 33.2 ⁢ ° ⁢   ⁢ ( 0.67 , 95 ⁢ % ⁢   ⁢ EtOH )

後処理

  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

出典と根拠

ORDレコード
ord-5567c6a16281438883569b9ccc38382a
出典データセット
uspto-grants-2005_02
特許番号
US06855820B2

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