Benzyl Bromide → HCID 69969640, compound

HRID 1280734Notes

Reaction equation

HRID 1280734 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([S:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[CH:10]([OH:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([OH:21])[CH:11]([S:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:18][CH:19]=2)[CH2:12]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 69969990HCID 69969990, compound

Product 1

HCID 69969640HCID 69969640, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(3RS,4RS)-3-Hydroxy-4-(4-hydroxy-phenylsulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.2 g, 0.6 mmol) was dissolved in acetone (5 ml), and treated with K2CO3 (0.1 g, 0.7 mmol). After 1 hour refluxing, the reaction mixture was cooled to room temperature and benzylbromide (0.084 ml, 0.7 mmol) was added. Reaction mixture was refluxed for an additional 3 hours then cooled to room temperature and quenched with H2O. The aqueous phase was extracted with CH2Cl2, the combined organic phases were dried over Na2SO4, filtered and the solvent was evaporated. The residue was chromatographed over silica gel (hexane-ethyl acetate 2:1) to provide (3RS,4RS)-3-(4-benzyloxy-phenylsulfanyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (0.208 g, 81%) as a yellow oil, MS: m/e=402.4 (M+H+).

Workup

  1. temperatureAfter 1 hour refluxing
  2. customReaction mixture
  3. temperaturewas refluxed for an additional 3 hours
  4. temperaturethen cooled to room temperature
  5. customquenched with H2O
  6. extractionThe aqueous phase was extracted with CH2Cl2
  7. dry with materialthe combined organic phases were dried over Na2SO4
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. customThe residue was chromatographed over silica gel (hexane-ethyl acetate 2:1)

Sources & evidence

ORD record
ord-597e591c505545fa86f79cf3e8e98c5c
Source dataset
uspto-grants-2002_09
Patent number
US06451819B2

Reaction notes

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