Water → (2R,4R)-1-benzyl-2-(2-hydroxyethyl)-4-(t-butyldimethylsilyloxy)pyrrolidine

HRID 975645Notes

Reaction equation

HRID 975645 reaction equation
[CH2:1]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@H:9]1[CH:21]=[CH2:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C12BC(CCC1)CCC2.O.B1([O-])O[O:34]1.O.O.O.O.[Na+]>O1CCCC1>[CH2:1]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:18])([CH3:20])[CH3:19])([CH3:15])[CH3:16])[CH2:10][C@H:9]1[CH2:21][CH2:22][OH:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 789669-Borabicyclo(3.3.1)nonaneHCID 11726876(2S,4R)-1-benzyl-2-vinyl-4-(t-butyldimethylsilyloxy)pyrrolidineHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrate

Product 1

HCID 54180959(2R,4R)-1-benzyl-2-(2-hydroxyethyl)-4-(t-butyldimethylsilyloxy)pyrrolidineYield 82.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2S,4R)-1-benzyl-2-vinyl-4-(t-butyldimethylsilyloxy)pyrrolidine (24.03 g) in tetrahydrofuran (120 ml) was added 0.5M solution of 9-borabicyclo[3.3.1]nonane in tetrahydrofuran (318 ml) at 0°~5° C. with stirring and then stirred at ambient temperature for 4 hours. To the reaction mixture were added water (200 ml) and sodium perborate tetrahydrate (87 g) at ambient temperature with stirring vigorously and then the mixture was stirred at the same temperature for 12 hours. The insoluble material was filtered off, and the filtrate was separated. The organic layer was dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel chromatography eluting with a mixture of n-hexane and ethyl acetate (1:1, V/V) to give (2R,4R)-1-benzyl-2-(2-hydroxyethyl)-4-(t-butyldimethylsilyloxy)pyrrolidine (20.89 g).

Workup

  1. stirringstirred at ambient temperature for 4 hours
  2. stirringwith stirring vigorously
  3. stirringthe mixture was stirred at the same temperature for 12 hours
  4. filtrationThe insoluble material was filtered off
  5. customthe filtrate was separated
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with a mixture of n-hexane and ethyl acetate (1:1, V/V)

Sources & evidence

ORD record
ord-123aa35c660c413fb775d8ea20ecb96f
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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