Water → HCID 22882478, compound

HRID 863290Notes

Reaction equation

HRID 863290 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]2([CH2:17][CH2:18][OH:19])[CH2:16][CH2:15]2)[CH2:11][O:10][C:9]1([CH3:21])[CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]2([CH2:17][CH2:18][O:19][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:16][CH2:15]2)[CH2:11][O:10][C:9]1([CH3:21])[CH3:20])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 82127Potassium hydrideHCID 22882479HCID 22882479, compound

Product 1

HCID 22882478HCID 22882478, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

15.1 g of 3-tert-butoxycarbonyl-2,2-dimethyl-4(S)-[1-(2-hydroxyethyl)cyclopropylmethyl]-1,3-oxazolidine are dissolved in 50 ml of tetrahydrofuran, and 14.2 g of a potassium hydride suspension (20% in oil) are added at 0° C. The mixture is stirred at 0° C. for 1 h and 6.3 ml of benzyl bromide are then added dropwise, while stirring. After 90 min., 100 ml of water are slowly added to the reaction mixture and the aqueous phase is extracted with diethyl ether. This gives the title compound: Rf (A)=0.8; FAB-MS: (M+H)+ =390.

Workup

  1. stirringwhile stirring
  2. waitAfter 90 min.
  3. extractionthe aqueous phase is extracted with diethyl ether

Sources & evidence

ORD record
ord-e2d3c66da1ce4034b1d41d6654284c16
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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