Sodium borohydride → HCID 178519876, compound

HRID 1598893Notes

Reaction equation

HRID 1598893 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][C:28]([OH:37])([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:27][CH2:26]2)[C:10]([C:12]2[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:14][NH:15][CH:16]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[BH4-].[Na+].CCOCC.CCCCCC>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:23][CH2:24][N:25]2[CH2:26][CH2:27][C:28]([OH:37])([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:29][CH2:30]2)[CH:10]([C:12]2[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:14][NH:15][CH:16]=2)[OH:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21584099Diethylether hexaneHCID 178519875HCID 178519875, compound

Product 1

HCID 178519876HCID 178519876, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-[2-(3,4-dichlorophenyl)-4-(4-hydroxy-4-phenylpiperidino)butyroyl]-3-phenyl-1H-pyrazole (95 mg), prepared as described in Example 3, in methanol (3 mL) was cooled to 0° C. and treated with sodium borohydride (9 mg). The mixture was allowed to warm to room temperature and was stirred for 1 hour. The solvent was evaporated and the residue partitioned between water and ethyl acetate. The organic extracts were washed (water, brine) combined, dried, and evaporated to afford a white foam. Trituration with ether:hexane (1:2) afforded the title compound as a white solid (62 mg); mp 133°-135° C.; NMR: 7.57-7.23 (m,13), 7.03 (m,1), 5.11 (d,1), 3.04 (m,1), 2.86 (m,2), 2.51 (m,2), 2.37 (m,2), 2.23 (m,2), 1.94 (m,1), 1.81-1.60 (m,3); MS: m/z=536(M+1). Analysis for C30H31 Cl2N3O2 ·1.00 H2O: Calculated: C, 64.98; H, 5.82; N, 7.83; Found: C, 64.91; H, 5.74; N, 7.53.

Workup

  1. temperatureto warm to room temperature
  2. customThe solvent was evaporated
  3. customthe residue partitioned between water and ethyl acetate
  4. washThe organic extracts were washed (water, brine)
  5. customdried
  6. customevaporated
  7. customto afford a white foam

Sources & evidence

ORD record
ord-28f54f775b90448191ca971d96c0f78c
Source dataset
uspto-grants-1998_04
Patent number
US05739149

Reaction notes

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