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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 271306
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HRID 271306 반응식
[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
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참가 물질

4

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HCID 4311764Sodium borohydrideHCID 178481818HCID 178481818, 화합물

생성물 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-sulfinamide수율 109%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f7e269e0506c43ab963371caaf3e2a2d
출처 데이터셋
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07452899B2

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