Hydrochloric Acid → [(4R,5R)-5-(4-methylsulfonylphenyl)-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl]methanol

HRID 1879336Notes

Reaction equation

HRID 1879336 reaction equation
C([O:3][C:4]([C@@H:6]1[C@@H:10]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[O:9][C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:7]1)=O)C.[BH4-].[K+].Cl.O>CO>[CH3:20][S:17]([C:14]1[CH:13]=[CH:12][C:11]([C@H:10]2[O:9][C:8]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:7][C@@H:6]2[CH2:4][OH:3])=[CH:16][CH:15]=1)(=[O:18])=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4192641Potassium borohydrideHCID 46831018(4S-trans)-4,5-dihydro-5-[4-(methylsulfonyl)phenyl]-2-phenyl-4-oxazolecarboxylic acid ethyl ester

Product 1

HCID 14760452[(4R,5R)-5-(4-methylsulfonylphenyl)-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl]methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(4S-trans)-4,5-Dihydro-5-[4-(methylsulfonyl)phenyl]-2-phenyl-4-oxazolecarboxylic acid ethyl ester (Compound IIIk) (about 5 g, 0.0134 moles) in methanol (about 50 mL) is reacted in a reaction vessel with potassium borohydride (about 1.1 g, 0.0201 moles) over about 6 hours while maintaining the temperature below about 60° C. The reaction is cooled to ambient room temperature and about 1N HCl (about 10 mL) and water (about 50 mL) are added. The resulting solids are filtered, washed with water, then dried to yield (4R,5R)-4,5-Dihydro-5-[4-(methylsulfonyl)phenyl]-2-phenyl-4-oxazolemethanol (Compound II wherein R1 is methylsulfonyl, R2 is phenyl and R3 is ethyl).

Workup

  1. temperaturewhile maintaining the temperature below about 60° C
  2. filtrationThe resulting solids are filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-7a6fb71739e2406fafd86c65e7bb3ab7
Source dataset
uspto-grants-2012_11
Patent number
US08314252B2

Reaction notes

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