(1S)-(+)-Camphor-10-sulphonic acid → (R)-3-[3-(3,4-Dichlorophenyl)-piperidin-3-yl]-propan-1-ol(1s)-7,7-dimethyl-2-oxobicyclo[2,2,1]heptane-1-methanesulfonate

HRID 394546ノート

反応式

HRID 394546 の反応式
[C@:1]12([CH2:11][S:12]([OH:15])(=[O:14])=[O:13])[C:8]([CH3:10])([CH3:9])[CH:5]([CH2:6][CH2:7]1)[CH2:4][C:2]2=[O:3].[Cl:16][C:17]1[CH:18]=[C:19]([C:24]2([CH2:30][CH2:31][CH2:32]O)[CH2:29][CH2:28][CH2:27][NH:26][CH2:25]2)[CH:20]=[CH:21][C:22]=1[Cl:23]>CC(O)C>[CH3:9][C:8]1([CH3:10])[CH:5]2[CH2:6][CH2:7][C@@:1]1([CH2:11][S:12]([O:15][CH2:32][CH2:31][CH2:30][C@@:24]1([C:19]3[CH:20]=[CH:21][C:22]([Cl:23])=[C:17]([Cl:16])[CH:18]=3)[CH2:29][CH2:28][CH2:27][NH:26][CH2:25]1)(=[O:13])=[O:14])[C:2](=[O:3])[CH2:4]2

参加物

4

反応物 2

HCID 218580(1S)-(+)-Camphor-10-sulphonic acidHCID 109350863-(3-(3,4-Dichlorophenyl)piperidin-3-YL)propan-1-OL

生成物 1

HCID 131724007(R)-3-[3-(3,4-Dichlorophenyl)-piperidin-3-yl]-propan-1-ol(1s)-7,7-dimethyl-2-oxobicyclo[2,2,1]heptane-1-methanesulfonate収率 104.9%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒2 回

実験手順

A solution of (S)-(+)-camphorsulfonic acid (10.3 g, 44.41 mmol) in iPrOH (10 mL) was added to a solution of hydroxy piperidine (8) (12.8 g, 44.41 mmol) in iPrOH. The mixture was heated to reflux for 15 minutes. The solvent was removed to give glassy solid 23.4 g, which solid was then recrystallized in iPrOH two times to give white crystals (5.5 g, 23.8%, 95% ee), mp 188-189° C.

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 15 minutes
  3. customThe solvent was removed

出典と根拠

ORDレコード
ord-b1e617ce115348f79c49a6d4f6eba35c
出典データセット
uspto-grants-2003_08
特許番号
US06602886B2

反応ノート

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