Benzyl Bromide → HCID 57870122, compound

HRID 1045682Notes

Reaction equation

HRID 1045682 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH2:16]([O:13][CH:10]1[CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 44169391-Boc-3-pyrrolidinol

Product 1

HCID 57870122HCID 57870122, compoundYield 110.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1-(tert-butoxycarbonyl)-3-hydroxy-pyrrolidine (430 mg, 2.30 mmol) in N,N-dimethylformamide (3 ml) was added to a solution of sodium hydride (60% dispersion in mineral oil, 137 mg, 3.43 mmol) and the mixture was stirred for one hour. A solution of benzyl bromide (562 mg, 3.29 mmol) in N,N-dimethylformamide (1 ml) was added to the solution and the mixture was stirred overnight. Reaction was quenched with water and the reaction mixture was extracted with diethyl ether. The organic layer was washed with water and dried over sodium sulfate. Removal of solvent afforded crude 3-benzyloxy-1-(tert-butoxycarbonyl)-pyrrolidine (705 mg).

Workup

  1. stirringthe mixture was stirred overnight
  2. customReaction
  3. customwas quenched with water
  4. extractionthe reaction mixture was extracted with diethyl ether
  5. washThe organic layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. customRemoval of solvent

Sources & evidence

ORD record
ord-a025af1a619e4648b228c2a0d7ce653e
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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