Sodium borohydride → HCID 68532412, compound

HRID 2180182Notes

Reaction equation

HRID 2180182 reaction equation
[C:1]([O:5][C:6](=[O:19])[N:7]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]([F:18])[CH:12]=1)[CH2:8][CH:9]=O)([CH3:4])([CH3:3])[CH3:2].[I:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2([CH2:34][NH2:35])[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]2)=[CH:23][CH:22]=1.[BH4-].[Na+]>CO>[C:1]([O:5][C:6](=[O:19])[N:7]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]([F:18])[CH:12]=1)[CH2:8][CH2:9][NH:35][CH2:34][C:27]1([C:24]2[CH:23]=[CH:22][C:21]([I:20])=[CH:26][CH:25]=2)[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 22490346HCID 22490346, compoundHCID 22490374HCID 22490374, compound

Product 1

HCID 68532412HCID 68532412, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of (3,4-difluorophenyl)-(2-oxo-ethyl)-carbamic acid-tert-butyl ester (1.23 g, 4.3 mmol) in MeOH (35 mL) under Ar at room temperature was added a solution of C-[4-(4-iodo-phenyl)-1-methyl-piperidin-4-yl]-methylamine (1.49 g, 4.5 mmol, 1.05 eq.) in MeOH (10 mL). The mixture was stirred at room temperature for 5 h then NaBH4 (0.255 g, 6.75 mmol, 1.5 eq) was added and the resulting mixture was stirred for a further 1 h and then was quenched by the addition of 1N aqueous NaOH (40 mL). The mixture was extracted twice with Et2O (2×50 mL) and the combined organic extracts were washed with saturated brine (100 mL) and dried over Na2SO4. Filtration and concentration of the filtrate by rotary evaporation gave the crude product which was purified by flash column chromatography by eluting with 12% EtOAc/hexanes to give (3,4-difluoro-phenyl)-(2-{[4-(4-iodo-phenyl)-1-methyl-piperidin-4-ylmethyl]-amino}-ethyl)-carbamic acid tert-butyl ester (2.03 g, 76%) as a pale oil. MS (ESI): 585.9/587.0 (M+H).

Workup

  1. stirringthe resulting mixture was stirred for a further 1 h
  2. customwas quenched by the addition of 1N aqueous NaOH (40 mL)
  3. extractionThe mixture was extracted twice with Et2O (2×50 mL)
  4. washthe combined organic extracts were washed with saturated brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationFiltration and concentration of the filtrate
  7. customby rotary evaporation
  8. customgave the crude product which
  9. customwas purified by flash column chromatography
  10. washby eluting with 12% EtOAc/hexanes

Sources & evidence

ORD record
ord-665f6e2d88714b22bce26db8c3624bdb
Source dataset
uspto-grants-2005_05
Patent number
US06887889B2

Reaction notes

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