Sodium borohydride → HCID 67061959, compound

HRID 337701Notes

Reaction equation

HRID 337701 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:26]=[C:27]([C:30](=[O:38])[C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=2)[C:28]=1[CH3:29])[CH2:5][N:6]([CH:23]1[CH2:25][CH2:24]1)[C:7]([C@H:9]1[C@H:14]([C:15]2[CH:20]=[CH:19][N:18]([CH3:21])[C:17](=[O:22])[CH:16]=2)[CH2:13][CH2:12][NH:11][CH2:10]1)=[O:8].[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:26]=[C:27]([CH:30]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=2)[OH:38])[C:28]=1[CH3:29])[CH2:5][N:6]([CH:23]1[CH2:25][CH2:24]1)[C:7]([C@H:9]1[C@H:14]([C:15]2[CH:20]=[CH:19][N:18]([CH3:21])[C:17](=[O:22])[CH:16]=2)[CH2:13][CH2:12][NH:11][CH2:10]1)=[O:8]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67062116HCID 67062116, compound

Product 1

HCID 67061959HCID 67061959, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a MeOH (0.09 M) solution of trans-N-[3-bromo-5-(3-fluorobenzoyl)-4-methylbenzyl]-N-cyclopropyl-4-(1-methyl-2-oxo-1,2-dihydro-4-pyridinyl)-3-piperidine-carboxamide (1 eq., Example 106) was added sodium borohydride (1.4 eq.). The resulting solution was stirred at RT for 15 h before the volatiles were removed in vacuo. The resulting residue carefully added 10% aq. HCl, followed by 1 N aq. NaOH so that the pH of the final solution is ˜10. After extraction with EtOAc, the combined organic extracts were washed further with brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Further purification by way of column chromatography (SiO2, 93:7 (v/v) CH2Cl2:2.0 M NH3 in MeOH) afforded the title compound as a mixture of diastereomers. MS (ESI+, M+H): 584.

Workup

  1. customwere removed in vacuo
  2. extractionAfter extraction with EtOAc
  3. washthe combined organic extracts were washed further with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customFurther purification by way of column chromatography (SiO2, 93:7 (v/v) CH2Cl2:2.0 M NH3 in MeOH)

Sources & evidence

ORD record
ord-a45b650c9e5240e8a658f0b73c4f21c8
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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