4-Toluenesulfonyl chloride → rac-toluene-4-sulfonic acid (1R*,2R*,4R*)-2-(2-hydroxy-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl)-ethyl ester

HRID 220292Notes

Reaction equation

HRID 220292 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1([OH:18])[CH2:9][CH:8]2[CH2:10][CH2:11][CH:5]1[CH:6]=[C:7]2[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[S:19](Cl)([C:22]1[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=1)(=[O:21])=[O:20].CCN(CC)CC>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1>[OH:18][C@@:4]1([CH2:3][CH2:2][O:1][S:19]([C:22]2[CH:28]=[CH:27][C:25]([CH3:26])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH2:9][C@H:8]2[CH2:10][CH2:11][C@@H:5]1[CH:6]=[C:7]2[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 68412881rac-(1R*,2R*,4R*)-2-(2-hydroxy-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol

Product 1

HCID 91466714rac-toluene-4-sulfonic acid (1R*,2R*,4R*)-2-(2-hydroxy-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl)-ethyl esterYield 86.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 227 mg of rac-(1R*,2R*,4R*)-2-(2-hydroxy-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol, 195 mg of Ts-Cl, 0.16 mL of NEt3 and 11 mg of DMAP in 3 mL toluene was stirred overnight at rt. The reaction mixture was quenched with water, the organic phase was separated, washed with brine and evaporated. The residue was purified by CC with Hept-EtOAc (6:4) to yield 0.32 g of oily rac-toluene-4-sulfonic acid (1R*,2R*,4R*)-2-(2-hydroxy-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl)-ethyl ester as yellowish oil.

Workup

  1. customThe reaction mixture was quenched with water
  2. customthe organic phase was separated
  3. washwashed with brine
  4. customevaporated
  5. customThe residue was purified by CC with Hept-EtOAc (6:4)

Sources & evidence

ORD record
ord-6c05beeb521c40d0ab05851cb2eabc71
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

Loading…