Water → HCID 19762709, compound

HRID 249032Notes

Reaction equation

HRID 249032 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:30])[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([C:20]34[CH2:29][CH:24]5[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]5)[CH2:21]3)[CH2:27]4)[CH:13]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+].O>CO>[OH:3][CH:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:30])[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([C:20]34[CH2:29][CH:24]5[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]5)[CH2:21]3)[CH2:27]4)[CH:13]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 19762691HCID 19762691, compound

Product 1

HCID 19762709HCID 19762709, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The amide obtained in Example 23, above, (0.9 g, 2 mmoles) is dissolved in methanol (25ml) and treated with 0.12 g (3 mmoles) of sodium borohydride. The mixture is stirred at ambient temperature for 2 days, poured into water and extracted with ether. The extracts are dried on magnesium sulfate, then the solvent is evaporated. The resulting residue is recrystallized in ethyl acetate to give N[4-[1-hydroxyethyl)phenyl]-3-(1-adamantyl)-4-methoxy benzamide (0.5 g, 66% yield) having a melting point of 207°-209° C.

Workup

  1. extractionextracted with ether
  2. customThe extracts are dried on magnesium sulfate
  3. customthe solvent is evaporated
  4. customThe resulting residue is recrystallized in ethyl acetate

Sources & evidence

ORD record
ord-6bf5a87904274f1d96bbc45f87284c68
Source dataset
uspto-grants-1993_05
Patent number
US05212203

Reaction notes

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