Acetic Acid → HCID 18672722, compound

HRID 1741094Notes

Reaction equation

HRID 1741094 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[N:12]=[C:11]([CH3:13])[O:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([N:22]2[C:30]3[CH:29]=[C:28]4[C:31]5([CH2:37][O:38][C:27]4=[CH:26][C:25]=3[CH2:24][CH2:23]2)[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]5)=[O:21])=[CH:16][CH:15]=1.[BH4-].[Na+].O.[OH-].[Na+].[C:44](O)(=O)[CH3:45]>>[CH2:44]([N:34]1[CH2:33][CH2:32][C:31]2([C:28]3[C:27](=[CH:26][C:25]4[CH2:24][CH2:23][N:22]([C:20]([C:17]5[CH:16]=[CH:15][C:14]([C:3]6[CH:4]=[CH:5][C:6]([C:8]7[N:12]=[C:11]([CH3:13])[O:10][N:9]=7)=[CH:7][C:2]=6[CH3:1])=[CH:19][CH:18]=5)=[O:21])[C:30]=4[CH:29]=3)[O:38][CH2:37]2)[CH2:36][CH2:35]1)[CH3:45]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 4311764Sodium borohydride2×HCID 18784692HCID 18784692, compound

Product 1

HCID 18672722HCID 18672722, compoundYield 52%

Procedure

A stirred solution of 5-(2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carbonyl)-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine] (E3, 100 mg, 0.20 mmole) in glacial acetic acid (2 ml) at room temperature under argon was carefully treated with sodium borohydride pellets (50 mg, 1.3 mmole) and stirred for 24 H. Additional sodium borohydride pellets were added (50 mg, 1.3 mmole) and reaction mixture stirred at room temperature for a further 72 h. The reaction mixture was then treated with water (20 ml), basified with 10% NaOH solution (20 ml) and extracted with dichloromethane. The extract was dried (Na2SO4), concentrated in vacuo and the residue chromatographed on silica gel eluting with 3% MeOH/CHCl3. Crystallisation of the product form ethyl acetate/60-80 petrol afforded the title compound as a white solid (55 mg, 52%) mp 202-204° C.

Workup

  1. custom(50 mg, 1.3 mmole) and reaction mixture
  2. stirringstirred at room temperature for a further 72 h
  3. extractionextracted with dichloromethane
  4. dry with materialThe extract was dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customthe residue chromatographed on silica gel eluting with 3% MeOH/CHCl3
  7. customCrystallisation of the product
  8. customform ethyl acetate/60-80 petrol

Sources & evidence

ORD record
ord-28ebde8fd2da46df85741366525720a2
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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