Ammonium Chloride → HCID 69286681, compound

HRID 2225302Notes

Reaction equation

HRID 2225302 reaction equation
[CH2:1]([N:8]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C@H:9]1[CH2:14][CH2:13][C@@H:12]([N:15]([CH:17]([CH3:19])[CH3:18])[CH3:16])[CH2:11][C@H:10]1[CH2:20][C:21](=[O:25])[CH:22]([CH3:24])[CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[NH4+].[Cl-].C([O-])(O)=O.[Na+]>CO>[CH2:1]([N:8]([CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C@H:9]1[CH2:14][CH2:13][C@@H:12]([N:15]([CH:17]([CH3:19])[CH3:18])[CH3:16])[CH2:11][C@H:10]1[CH2:20][CH:21]([OH:25])[CH:22]([CH3:23])[CH3:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 69286603HCID 69286603, compound

Product 1

HCID 69286681HCID 69286681, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Examples 11p and 11q, Step 8: To a solution of 1-((1S,2S,5R)-2-(dibenzylamino)-5-(isopropyl(methyl)amino)cyclohexyl)-3-methylbutan-2-one (168 mg, 0.39 mmoles) in 3 ml of methanol was added sodium borohydride (29.2 mg, 0.78 mmoles), the mixture was stirred for 2 hours at room temperature. At the end of the stirring was added saturated NH4Cl, and then the mixture was made basic with saturated NaHCO3. It was extracted with EtOAc, washed with brine, dried over Na2SO4, and evaporated to give 166 mg of 1-((1S,2S,5R)-2-(dibenzylamino)-5-(isopropyl(methyl)amino)cyclohexyl)-3-methylbutan-2-ol as a mixture of the two isomers (ratio ˜2:1).

Workup

  1. extractionIt was extracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-2187cb36fad549b7875716cb1921dc02
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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