Sodium Thiosulfate → Benzyl (1R*,3S*,4R)-3,4-epoxycyclohexane-1-carboxylate

HRID 459516Notes

Reaction equation

HRID 459516 reaction equation
[CH:1]1([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:25])C=1.S([O-])([O-])(=[O:30])=S.[Na+].[Na+]>ClCCl>[O:25]1[C@H:4]2[C@@H:3]1[CH2:2][C@H:1]([C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8])[CH2:6][CH2:5]2.[O:30]1[C@@H:4]2[C@H:3]1[CH2:2][C@H:1]([C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8])[CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 11020300Benzyl 3-cyclohexene-1-carboxylate

Product 2

HCID 57432601Benzyl (1R*,3S*,4R)-3,4-epoxycyclohexane-1-carboxylateHCID 57481684benzyl (1R*,3R*,4S*)-3,4-epoxycyclohexane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl (±)-3-cyclohexene-1-carboxylate (40 g) was dissolved in dichloromethane (500 ml), and m-chloroperbenzoic acid (86 g) was added under ice cooling to stir the mixture for 2 hours. After a 10% aqueous solution of sodium thiosulfate was added to conduct stirring for 20 minutes, an organic layer was separated, washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:9) to obtain the title compound (23.4 g) and benzyl (1R*,3R*,4S*)-3,4-epoxycyclohexane-1-carboxylate (12.1 g) as colorless oils.

Workup

  1. stirringto conduct stirring for 20 minutes
  2. customan organic layer was separated
  3. washwashed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:9)

Sources & evidence

ORD record
ord-d08c7085aa574b5cb3265a2cb5b02a9c
Source dataset
uspto-grants-2007_03
Patent number
US07192968B2

Reaction notes

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