Acetic Acid → HCID 66704852, compound

HRID 859882Notes

Reaction equation

HRID 859882 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[C@@H:13]([CH2:24][O:25][Si](C(C)(C)C)(C)C)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C(O)(=O)C>O1CCCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][Si:17]([C:20]([CH3:21])([CH3:22])[CH3:23])([CH3:19])[CH3:18])[C@@H:13]([CH2:24][OH:25])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 68820224HCID 68820224, compound

Product 1

HCID 66704852HCID 66704852, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(3R,4R)-1-Benzyloxycarbonyl-3-(tert-butyldimethylsilyl)oxymethyl-4-(tert-butyldimethylsilyl)oxypyrrolidine (5.46 g) was dissolved in tetrahydrofuran (23 mL). While this solution was cooled on an ice bath, water (23 mL) and acetic acid (68 mL) were sequentially added and the mixture was stirred at room temperature for 8 hours. Subsequently, the reaction mixture was concentrated under reduced pressure and the resulting residue was purified on a silica gel column (eluant=hexane:ethyl acetate=4:1 shifted to 1:1) to give 2.74 g of (3R,4R)-1-benzyloxycarbonyl-3-hydroxymethyl-4-(tert-butyldimethylsilyloxy)pyrrolidine as a colorless oil.

Workup

  1. temperatureWhile this solution was cooled on an ice bath
  2. concentrationSubsequently, the reaction mixture was concentrated under reduced pressure
  3. customthe resulting residue was purified on a silica gel column (eluant=hexane:ethyl acetate=4:1 shifted to 1:1)

Sources & evidence

ORD record
ord-e41957bc92dd461d80580d45211c0b30
Source dataset
uspto-grants-2006_12
Patent number
US07153851B2

Reaction notes

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