Cyclohexylamine → 4-(4'-Chloro-2'-methyl-4-biphenylyl)-4-hydroxy-butyric acid

HRID 2397414Notes

Reaction equation

HRID 2397414 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:20])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=2)=[C:4]([CH3:21])[CH:3]=1.[BH4-].[Na+].C1(N)CCCCC1>C(Cl)CCl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH:14]([OH:20])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:12][CH:13]=2)=[C:4]([CH3:21])[CH:3]=1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 4311764Sodium borohydrideHCID 214379704-(4'-Chloro-2'-methyl-4-biphenylyl)-4-oxo-butyric acid

Product 1

HCID 214379944-(4'-Chloro-2'-methyl-4-biphenylyl)-4-hydroxy-butyric acidYield 96%

Reagents, catalysts & solvents 1

HCID 20136152Ethylene chloride ethyl acetateSolvent

Procedure

Prepared analogous to Example 25 by reduction of 4-(4'-chloro-2'-methyl-4-biphenylyl)-4-oxo-butyric acid (m.p. 153°-154° C.) with sodium borohydride. Yield: 96%. Melting point of the cyclohexylamine salt: 139°-140° C. (from ethylene chloride/ethyl acetate 5:1).

Sources & evidence

ORD record
ord-83a3eb6f20af4a248e1f8d6a61e185bb
Source dataset
uspto-grants-1977_05
Patent number
US04021479

Reaction notes

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