Sodium borohydride → HCID 178509566, compound

HRID 1249961Notes

Reaction equation

HRID 1249961 reaction equation
[O:1]=[CH:2][CH2:3][CH2:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.[BH4-].[Na+]>CO.CCOCC>[OH:1][CH2:2][CH2:3][CH2:4][C@H:5]1[CH2:6][CH2:7][C@H:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:18]=[CH:19][C:20]([C:23]#[N:24])=[CH:21][CH:22]=3)=[CH:13][CH:12]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 178509565HCID 178509565, compound

Product 1

HCID 178509566HCID 178509566, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 21864698Diethyl ether methanolSolvent2×

Procedure

A solution of 12 g of trans-4′-[4-(3-oxo-propyl)-cyclohexyl]-biphenyl-4-carbonitrile (preparation: Mol. Cryst. Liq. Cryst. 1985, Vol. 131, 327) in 100 ml methanol/ether (9:1) was added dropwise at 0° C. within 5 minutes to a suspension of 1.39 g of sodium borohydride in 30 ml of methanol/ether (9:1). After 45 minutes a further 1 g of sodium borohydride was added. After a further hour the reaction was interrupted and the mixture was partitioned between methylene chloride and 1N hydrochloric acid. Thereupon, the organic phase was washed several times with water, dried over magnesium sulphate, filtered and evaporated. Crystallization from ethyl acetate/methylene chloride gave 11.5 g of trans-4′-[4-(3-hydroxy-propyl)-cyclohexyl]-biphenyl-4-carbonitrile as yellowish crystals.

Workup

  1. waitAfter a further hour the reaction was interrupted
  2. customthe mixture was partitioned between methylene chloride and 1N hydrochloric acid
  3. washThereupon, the organic phase was washed several times with water
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customCrystallization from ethyl acetate/methylene chloride

Sources & evidence

ORD record
ord-a70205a935664216a0f2171a3e7285ad
Source dataset
uspto-grants-2002_01
Patent number
US06335409B1

Reaction notes

Loading…