Hydrochloric Acid → HCID 178418591, compound

HRID 5308Notes

Reaction equation

HRID 5308 reaction equation
[BH4-].[Na+].[CH3:3][C@@H:4]([O:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([CH:26]3[CH2:31][CH2:30][C:29](=[O:32])[CH2:28][CH2:27]3)=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)=[O:13])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].Cl>COCCOC>[CH3:3][C@@H:4]([O:11][C:12]([C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C@H:26]3[CH2:27][CH2:28][C@H:29]([OH:32])[CH2:30][CH2:31]3)=[CH:22][CH:21]=2)=[CH:18][CH:19]=1)=[O:13])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 566176494-(4'-[(R)-2-octyl]oxycarbonyl-4-biphenylyl)cyclohexanone

Product 1

HCID 178418591HCID 178418591, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A suspension of 0.14 g of sodium borohydride in 10 ml of 1,2-dimethoxyethane was treated at 0° C. with a solution of 4-(4'-[(R)-2-octyl]oxycarbonyl-4-biphenylyl)cyclohexanone in 10 ml of 1,2-dimethoxyethane. The reaction mixture was stirred at room temperature for a further 30 minutes and then treated with 25% hydrochloric acid. The reaction mixture was extracted three times with 50 ml of diethyl ether each time. The combined organic phases were washed with sodium hydrogen carbonate solution and several times with water and subsequently dried over magnesium sulfate, filtered and concentrated. The residue was recrystallized twice from hexane and gave 0.8 g of trans-4-(4'-[(R)-2-octyl]oxycarbonyl 4-biphenylyl)cyclohexanol.

Workup

  1. extractionThe reaction mixture was extracted three times with 50 ml of diethyl ether each time
  2. washThe combined organic phases were washed with sodium hydrogen carbonate solution and several times with water
  3. dry with materialsubsequently dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was recrystallized twice from hexane

Sources & evidence

ORD record
ord-3f2f18a0c6a1488a9177a1834c0193c2
Source dataset
uspto-grants-1993_09
Patent number
US05244597

Reaction notes

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