Benzyl Bromide → HCID 53877280, compound

HRID 847311Notes

Reaction equation

HRID 847311 reaction equation
[CH:1]1([CH2:7][CH:8]2[CH:12]([CH2:13][CH:14]([CH:18]([CH3:20])[CH3:19])[CH2:15][CH2:16]O)[O:11][C:10]([CH3:22])([CH3:21])[N:9]2[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:30].[Na+].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1(C)C=CC=CC=1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:32]([O:30][C@@:14]([CH:18]([CH3:19])[CH3:20])([CH2:15][CH3:16])[CH2:13][C@@H:12]1[O:11][C:10]([CH3:21])([CH3:22])[N:9]([C:23]([O:25][C:26]([CH3:28])([CH3:29])[CH3:27])=[O:24])[C@H:8]1[CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 19882234HCID 19882234, compound

Product 1

HCID 53877280HCID 53877280, compoundYield 78.5%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

A mixture of 500 mg (1.2 mmol) of t-butyl 4-(cyclohexylmethyl)-5-(4-hydroxy-2-isopropylbutyl)-2,2-dimethyl-3-oxazolidinecarboxylate in 3 ml of toluene, 191 mg (0.5 mmol) of tetrabutylammonium iodide, 5.9 g (150 mmol) of sodium hydroxide in water (8.8 ml) and 1.16 ml (9.8 mmol) of benzyl bromide is stirred at room temperature for 24 hours. Thereafter, water is added thereto, the mixture is extracted with ether, the ether extracts are dried over sodium sulphate and evaporated to dryness under reduced pressure. Chromatography of the residue on silica gel with a 1:8 mixture of ether and petroleum ether yields 457 mg (78.5%) of t-butyl (4S,5S)-5-[(S)-2-(benzyloxy)-2-isopropylbutyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylate as a pale yellow resin, MS: 486 (M-CH3)+.

Workup

  1. extractionthe mixture is extracted with ether
  2. dry with materialthe ether extracts are dried over sodium sulphate
  3. customevaporated to dryness under reduced pressure
  4. additionChromatography of the residue on silica gel with a 1:8 mixture of ether and petroleum ether

Sources & evidence

ORD record
ord-33386f0c281142a7afb35fa50d912ce7
Source dataset
uspto-grants-1992_08
Patent number
US05140011

Reaction notes

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