Benzyl Bromide → (2S,4R)-2-benzyloxymethyl-4-tert-butoxy-1-(naphthalene-2-sulfonyl)-pyrrolidine

HRID 1006837Notes

Reaction equation

HRID 1006837 reaction equation
[H-].[Na+].[C:3]([O:7][C@H:8]1[CH2:12][N:11]([S:13]([C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=2)(=[O:15])=[O:14])[C@H:10]([CH2:26][OH:27])[CH2:9]1)([CH3:6])([CH3:5])[CH3:4].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CS(C)=O>[CH2:28]([O:27][CH2:26][C@@H:10]1[CH2:9][C@@H:8]([O:7][C:3]([CH3:6])([CH3:5])[CH3:4])[CH2:12][N:11]1[S:13]([C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=1)(=[O:15])=[O:14])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 69429584(2S,4R)-[4-tert-butoxy-1-(naphthalene-2-sulfonyl)-pyrrolidin-2-yl]-methanol

Product 1

HCID 69433315(2S,4R)-2-benzyloxymethyl-4-tert-butoxy-1-(naphthalene-2-sulfonyl)-pyrrolidine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

R2-ether formation: To a slurry of sodium hydride (60% in mineral oil, 2.75 g) in DMSO (100 ml) were added (2S,4R)-[4-tert-butoxy-1-(naphthalene-2-sulfonyl)-pyrrolidin-2-yl]-methanol (11.2 g) in portions within 0.5 h and benzyl bromide (7.2 ml) dropwise within 0.5 h at 20° C. The reaction mixture was stirred at room temperature for 1.5 h, poured onto ice/water and extracted with EtOAc. The organic phases were washed with water and brine, dried over magnesium sulphate and concentrated. The residue was crystallized from acetone/Et2O/hexane to obtain (2S,4R)-2-benzyloxymethyl-4-tert-butoxy-1-(naphthalene-2-sulfonyl)-pyrrolidine (10.05 g) as a colorless solid, mp 101-103° C., MS: 454 (MH+).

Workup

  1. additionpoured onto ice/water
  2. extractionextracted with EtOAc
  3. washThe organic phases were washed with water and brine
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated
  6. customThe residue was crystallized from acetone/Et2O/hexane

Sources & evidence

ORD record
ord-36d0d726adee408e9d5929cdd5b94f8f
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

Loading…