Ammonium Chloride → 1-(4-(2-Hydroxy-3-(4-(naphthalen-2-yl)piperidino)-propyloxy)benzo(b)furan-2-yl)ethanol

HRID 460638Notes

Reaction equation

HRID 460638 reaction equation
C(O)(=O)/C=C\C(O)=O.[CH3:9][C:10]([C:12]1[O:16][C:15]2[CH:17]=[CH:18][CH:19]=[C:20]([O:21][CH2:22][C@@H:23]([OH:41])[CH2:24][N:25]3[CH2:30][CH2:29][CH:28]([C:31]4[CH:40]=[CH:39][C:38]5[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=5)[CH:32]=4)[CH2:27][CH2:26]3)[C:14]=2[CH:13]=1)=[O:11].[BH4-].[Na+].[Cl-].[NH4+]>CO>[OH:41][CH:23]([CH2:24][N:25]1[CH2:26][CH2:27][CH:28]([C:31]2[CH:40]=[CH:39][C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH:32]=2)[CH2:29][CH2:30]1)[CH2:22][O:21][C:20]1[C:14]2[CH:13]=[C:12]([CH:10]([OH:11])[CH3:9])[O:16][C:15]=2[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 69497711(S)-4-(2-hydroxy-3-(4-(naphthalen-2-yl)piperidino)-propyloxy)benzo(b)furan-2-yl methyl ketone maleate

Product 1

HCID 227291291-(4-(2-Hydroxy-3-(4-(naphthalen-2-yl)piperidino)-propyloxy)benzo(b)furan-2-yl)ethanolYield 100.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-4-(2-Hydroxy-3-(4-(naphthalen-2-yl)piperidino)propyloxy)benzo(b)furan-2-yl methyl ketone (0.30 g) obtained in Example 56 was dissolved in methanol and sodium borohydride (30 mg) was added at room temperature. The mixture was stirred for 20 min. To the reaction mixture was added saturated aqueous ammonium chloride solution and the solvent was evaporated under reduced pressure. The obtained residue was dissolved in ethyl acetate, and the mixture was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (0.24 g) as brown crystals, melting point 143–144° C.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionThe obtained residue was dissolved in ethyl acetate
  3. washthe mixture was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-75f2780792cc4a88a7a544e5f4e4fedc
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

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