(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 394546노트

반응식

HRID 394546 반응식
[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

참가 물질

4

반응물 2

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

생성물 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-methanesulfonate수율 104.9%

시약·촉매·용매 1

HCID 3776Isopropanol용매2회

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-b1e617ce115348f79c49a6d4f6eba35c
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06602886B2

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