(+-)-2-Butanol → HCID 70246612, compound

HRID 1978904Notes

Reaction equation

HRID 1978904 reaction equation
C(O[C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11]([CH3:19])([C:15]([F:18])([F:17])[F:16])[O:10][CH2:9][CH2:8]2)(=O)C.C([OH:24])(CC)C.C(OC1C=C2C(=CC=1)[C@](C)(C(F)(F)F)OCC2)(=O)C>CCCCCC>[OH:24][CH:8]1[C:7]2[C:12](=[CH:13][CH:14]=[CH:5][CH:6]=2)[C@@:11]([CH3:19])([C:15]([F:18])([F:17])[F:16])[O:10][CH2:9]1

Participants

5

Reactant 3

HCID 6568(+-)-2-ButanolHCID 21202087HCID 21202087, compoundHCID 53638549HCID 53638549, compound

Product 1

HCID 70246612HCID 70246612, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of racemic 6-acetoxy-1-methyl-1-trifluoromethylisochroman (38.4 g, 0.140 mol), 10% sec-butanol solution in hexane (1.3 L), and lipase PS (35 g) was stirred vigorously at room temperature for 23 hr. After filtration, the filtrate was concentrated under reduced pressure to give a mixture. This was purified by silica-gel column chromatography eluted with gradient of hexane and ethyl acetate (15:1,5:1,2:1) to give, first, (1R)6-acetoxy-1-methyl-1-trifluoromethyl-isochroman as a colorless oil (17.3 g, 45%, 94%ee). The 1H-NMR spectra of this compound was identical with that of racemate. The second fraction gave (1S)-4-hydroxy-1-methyl-1-trifluoromethyl-isochroman as crystals (16.9 g, 52%, 83%ee). The 1H-NMR spectra of this material was identical with that of racemate.

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give a mixture
  4. customThis was purified by silica-gel column chromatography
  5. washeluted with gradient of hexane and ethyl acetate (15:1,5:1,2:1)
  6. customto give

Sources & evidence

ORD record
ord-6c47b329b95a4028a6f2c57407e22f41
Source dataset
uspto-grants-2001_05
Patent number
US06239147B1

Reaction notes

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