Sulfuric Acid → 2(R)-(p-tert-butyl-benzyl)-3-methyl-butanol

HRID 1779778Notes

Reaction equation

[CH:1]([C@@H:4]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:23][CH:22]=1)[C:5](N1[C@H](CC2C=CC=CC=2)COC1=O)=[O:6])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OCC)(=O)C.S(=O)(=O)(O)O>O1CCCC1.O1CCCC1.O>[CH:1]([C@@H:4]([CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]([CH3:29])([CH3:28])[CH3:30])=[CH:25][CH:26]=1)[CH2:5][OH:6])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

With stirring at 0° C., a solution of 8.63 g of 3-[2(R)-isopropyl-3-(p-tert-butyl-phenyl)-propanoyl]-4(R)-benzyl-oxazolidin-2-one in 40 ml of tetrahydrofuran is added dropwise to a suspension of 2.41 g of LiAlH4 in 160 ml of tetrahydrofuran. The reaction mixture is stirred for a further 4 hours at 0° C. and then, at 0° C., 5 ml of ethyl acetate, 30 ml of a mixture of tetrahydrofuran/water=1:1 and then 80 ml of 2N sulfuric acid are added in succession thereto. The suspension is extracted with ethyl acetate and the extracts are concentrated by evaporation and purified by FC (700 g of silica gel, eluant: dichloromethane). The title compound is obtained: Rf (dichloromethane)=0.34; m.p.=49°-51° C.

Workup

stirringThe reaction mixture is stirred for a further 4 hours at 0° C.
extractionThe suspension is extracted with ethyl acetate
concentrationthe extracts are concentrated by evaporation
custompurified by FC (700 g of silica gel, eluant: dichloromethane)

Sources & evidence

ORD record: ord-16706f00ccd14632ab2014f968b2dc9b
Source dataset: uspto-grants-1997_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05627182

Reaction notes

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