Benzyl Bromide → HCID 69430665, compound

HRID 1006852Notes

Reaction equation

HRID 1006852 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH:5]1[CH2:9][N:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH2:7][CH:6]1[CH2:14][OH:15].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[CH2:16]([O:15][CH2:14][CH:6]1[CH2:7][N:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH2:9][CH:5]1[CH2:4][OH:3])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 69433610HCID 69433610, compound

Product 1

HCID 69430665HCID 69430665, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-12 °C

Procedure

To a suspension of 60% NaH (66 mg, 1.64 mmol) in DMF (3 ml) was added a solution of ([3RS,4RS]-4-hydroxymethyl-1-methanesulfonyl-pyrrolidin-3-yl)-methanol (327 mg, 1.56 mmol) in DMF (5 ml) at −12° C. After 5 min, benzylbromide (286 mg, 1.64 mmol) was added and the mixture was stirred at −12° C. for 30 min. The mixture was allowed to warm to room temperature. The solvent was evaporated. Water was added and extracted with dichloromethane. The organic phase was dried, filtered and evaporated. Flash chromatography (hexane/EtOAc 2:1=>1:1) gave 275 mg (58%) of ([3RS,4RS]-4-benzyloxymethyl-1-methanesulfonyl-pyrrolidin-3-yl)-methanol as a colorless oil, MS: 358 (M+OAc)−.

Workup

  1. temperatureto warm to room temperature
  2. customThe solvent was evaporated
  3. additionWater was added
  4. extractionextracted with dichloromethane
  5. customThe organic phase was dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-c8ad95568d614f15ab5fb0865d9c3d21
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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