Sodium borohydride → HCID 68120077, compound

HRID 2072489Notes

Reaction equation

HRID 2072489 reaction equation
Cl.[F:2][C:3]([F:34])([F:33])[C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[CH:9]([CH2:15][N:16]1[CH2:32][CH2:31][C:19]3([N:23]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:22][NH:21][C:20]3=[O:30])[CH2:18][CH2:17]1)[CH2:8][CH2:7]2.[BH4-].[Na+]>CO.O>[F:33][C:3]([F:2])([F:34])[C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]([OH:14])[CH:9]([CH2:15][N:16]1[CH2:32][CH2:31][C:19]3([N:23]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH2:22][NH:21][C:20]3=[O:30])[CH2:18][CH2:17]1)[CH2:8][CH2:7]2

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 131710914HCID 131710914, compound

Product 1

HCID 68120077HCID 68120077, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

8-[(6-(Trifluoromethyl)-1,2,3,4-tetrahydro-1-oxo-2-naphthal-enyl)methyl]-1-phenyl-1,3,8,-triazaspiro[4.5]decan-4-one, hydrochloride (1:1) (0.65 g, see example 184) is slurried in methanol (10 ml) and, with cooling, treated with a solution of sodium borohydride (0.27 g) in water (2 ml). The resulting mixture is stirred at room temperature under nitrogen for 16 hours, diluted with water (10 ml), and extracted with methylene chloride. Concentration of the dried organic solution followed by trituration with absolute ethanol yields the free base of the title alcohol as a tan powder (0.5 g), melting point 238°-240° C.

Workup

  1. temperaturewith cooling
  2. extractionextracted with methylene chloride

Sources & evidence

ORD record
ord-edbde72a00c14ebca987a4dd3d9bcde7
Source dataset
uspto-grants-1977_09
Patent number
US04051248

Reaction notes

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