Sodium borohydride → HCID 53827185, compound

HRID 2072468Notes

Reaction equation

HRID 2072468 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9](=[O:15])[CH:8]([CH2:16][N:17]1[CH2:33][CH2:32][C:20]3([N:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH2:23][NH:22][C:21]3=[O:31])[CH2:19][CH2:18]1)[CH2:7]2.[BH4-].[Na+]>CO.O>[OH:15][C@@H:9]1[C:10]2[C:6](=[CH:5][C:4]([O:3][CH3:2])=[C:12]([O:13][CH3:14])[CH:11]=2)[CH2:7][C@H:8]1[CH2:16][N:17]1[CH2:18][CH2:19][C:20]2([N:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:23][NH:22][C:21]2=[O:31])[CH2:32][CH2:33]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 131710906HCID 131710906, compound

Product 1

HCID 53827185HCID 53827185, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

8-[(2,3-Dihydro-5,6-dimethoxy-1-oxo-1H-inden-2-yl)methyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one, hydrochloride (1:1) (20.0 g finely ground) is slurried in methanol (400 ml), cooled in ice, and treated dropwise with an excess of sodium borohydride dissolved in water (75 ml). The resulting mixture is stirred for 16 hours at room temperature. Dilution with water (400 ml), extraction with methylene chloride, and concentration of the dried methylene chloride extracts in vacuo yield the crude product. Crystallization of this material from absolute ethanol yields 13.3 g of isomerically pure title compound, melting point 189°-190° C.

Workup

  1. temperaturecooled in ice
  2. extractionDilution with water (400 ml), extraction with methylene chloride, and concentration of the dried methylene chloride extracts in vacuo
  3. customyield the crude product
  4. customCrystallization of this material from absolute ethanol

Sources & evidence

ORD record
ord-b67879c049ac4dfb8c194cdc06d2aa79
Source dataset
uspto-grants-1977_09
Patent number
US04051248

Reaction notes

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