Sodium Hydroxide → HCID 67663767, compound

HRID 1379126Notes

Reaction equation

HRID 1379126 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([OH:16])[C@H:13]([OH:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].[OH-:27].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[C:23]([O:22][C:20]([CH2:19][O:17][C@H:13]1[C@@H:14]([O:16][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:27])[CH2:15][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:12]1)=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 14771965HCID 14771965, compound

Product 1

HCID 67663767HCID 67663767, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Procedure

237 mg of cis-N-benzyloxycarbonylpyrrolidine-3,4-diol, 1 ml of t-butyl bromoacetate and 100 mg of tetrabutyl-ammonium hydrogen sulphate in 10 ml of toluene are stirred with 10 ml of 50% sodium hydroxide solution under phase transfer conditions. The organic phase is washed with water and evaporated. Chromatography of the evaporation residue on silica gel with ethyl acetate/hexane (1:3) gives 354 mg of benzyl cis-3,4-bis-t-butoxycarbonylmethoxy-pyrrolidine-1-carboxylate. MS: 354 (M-111).

Workup

  1. washThe organic phase is washed with water
  2. customevaporated

Sources & evidence

ORD record
ord-8a95d25b488645908d77d4d70f37aeb9
Source dataset
uspto-grants-1997_09
Patent number
US05670515

Reaction notes

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