(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 394546Notes

Reaction equation

HRID 394546 reaction equation
[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

Participants

4

Reactant 2

HCID 218580(1S)-(+)-Camphor-10-sulphonic acidHCID 109350863-(3-(3,4-DICHLOROPHENYL)PIPERIDIN-3-YL)PROPAN-1-OL

Product 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-methanesulfonateYield 104.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-b1e617ce115348f79c49a6d4f6eba35c
Source dataset
uspto-grants-2003_08
Patent number
US06602886B2

Reaction notes

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