Sodium borohydride → N(3-chloro-4-{(E)2-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]vinyl}bicyclo[4.2.1]non-3-en-9-yl)-2-methylpropane-2-sulfinamide

HRID 271306Notes

Reaction equation

HRID 271306 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH2:5][CH:6]2[CH2:7][CH2:8][CH:9](/[C:27]/2=[N:28]/[S:29]([C:31]([CH3:34])([CH3:33])[CH3:32])=[O:30])[CH2:10][C:11]=1/[CH:12]=[CH:13]/[C:14]1[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[N:16]([CH3:26])[N:15]=1>CO>[Cl:3][C:4]1[CH2:5][CH:6]2[CH:27]([NH:28][S:29]([C:31]([CH3:34])([CH3:33])[CH3:32])=[O:30])[CH:9]([CH2:10][C:11]=1/[CH:12]=[CH:13]/[C:14]1[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[N:16]([CH3:26])[N:15]=1)[CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178481818HCID 178481818, compound

Product 1

HCID 69308312N(3-chloro-4-{(E)2-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]vinyl}bicyclo[4.2.1]non-3-en-9-yl)-2-methylpropane-2-sulfinamideYield 109%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (0.83 g, 22 mmol) was added portionwise into a stirring solution of the product of Step 4 (5.19 g, 11 mmol) in methanol (150 ml) at 0° C. The mixture was stirred at 0° C. for 1 hr and then at ambient temperature for a further 2 hrs. The reaction mixture was concentrated in vacuo and diluted with water and extracted with ethyl acetate (3×100 ml). The organic extract was washed with brine, dried over MgSO4 and concentrated in vacuo to afford N(3-chloro-4-{(E)2-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]vinyl}bicyclo[4.2.1]non-3-en-9-yl)-2-methylpropane-2-sulfinamide (5.71 g, 79%). δH (400 MHz, CDCl3) 1.20-1.27 (9H, m), 1.86-1.91 (2H, m), 2.40-2.50 (1H, m), 2.56-2.67 (4H, m), 3.06-3.18 (1H, m), 3.30-3.39 (1H, m), 3.67-3.77 (2H, m), 3.82 (3H, s), 6.47 (1H, d, J 5.5), 6.63 (1H, d, J 16.0), 7.15 (2H, t, J, 8.5), 7.38-7.42 (2H, m), 7.47 (1H, d, J 16.0).

Workup

  1. waitat ambient temperature for a further 2 hrs
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate (3×100 ml)
  5. extractionThe organic extract
  6. washwas washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f7e269e0506c43ab963371caaf3e2a2d
Source dataset
uspto-grants-2008_11
Patent number
US07452899B2

Reaction notes

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