Boron trifluoride etherate → HCID 56609330, compound

HRID 2371405Notes

Reaction equation

HRID 2371405 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][Si](C(C)(C)C)(C)C)[CH2:13][C@H:12]1[CH2:24][O:25][C:26](=[O:28])[CH3:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(F)(F)F.CCOCC>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([OH:16])[CH2:13][C@H:12]1[CH2:24][O:25][C:26](=[O:28])[CH3:27])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 56624892HCID 56624892, compound

Product 1

HCID 56609330HCID 56609330, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4R)-1-benzyloxycarbonyl-2-acetoxymethyl-4-t-butyldimethylsilyloxypyrrolidine (42.23 g) in dry dichloromethane (422 ml), boron trifluoride etherate (103.54 g) was added at room temperature, and the resultant mixture was stirred at the same temperature for 4 hours. The reaction mixture was washed successively with aqueous sodium bicarbonate solution and water and dried over magnesium sulfate. Removal of the solvent gave (2S,4R)-1-benzyloxycarbonyl-2-acetoxymethyl-4-hydroxypyrrolidine.

Workup

  1. washThe reaction mixture was washed successively with aqueous sodium bicarbonate solution and water
  2. dry with materialdried over magnesium sulfate
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-8105108a0d5648218e02aa15951f605f
Source dataset
uspto-grants-1992_03
Patent number
US05093328

Reaction notes

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