Acetic Acid → 78867-61-5

HRID 1977595

반응식

HRID 1977595 반응식
[CH2:1]1[C@H:6]2[C:7]3[N:13]([CH2:14][C@@H:2]1[CH2:3][NH:4][CH2:5]2)[C:11](=[O:12])[CH:10]=[CH:9][CH:8]=3.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:1]1[C@H:6]2[C:7]3[N:13]([CH2:14][C@@H:2]1[CH2:3][N:4]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:5]2)[C:11](=[O:12])[CH:10]=[CH:9][CH:8]=3

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 10235CytisineHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 87291278867-61-5수율 58%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a 25 ml round bottom flask was added 0.510 gm (2.68 mmol) cytisine in 10 ml of 1,2-dichloroethane. The above solution was treated with 0.272 ml (2.68 mmol) benzaldehyde, 153 μl acetic acid and 0.852 gm (4.02 mmol) sodium triacetoxyborohydride. The reaction mixture was stirred at room temperature for 2 hours and was then partitioned between methylene chloride and 1 N HCl (aq). The organic phase was washed with brine, dried and the solvent evaporated in vacuo to a solid. Chromatography on silica gel eluting with 1% methanol in methylene chloride afforded 434 mg (58%) of the title product which was used in the next step. 1H NMR (CDCl3, 250 MHz) δ 7.28 (dd, 1H), 7.15 (m, 3H), 6.98 (m, 2H), 6.98 (m, 2H), 6.52 (d, 1H), 5.92 (d, 1H), 4.10 (d, 1H), 3.88 (dd, 1H), 3.40 (dd, 2H), 2.88 (m, 3H), 2.39 (br.s, 1H), 2.3 (dd, 2H), 1.82 (dd, 2H) ppm.

후처리

  1. customwas then partitioned between methylene chloride and 1 N HCl (aq)
  2. washThe organic phase was washed with brine
  3. customdried
  4. customthe solvent evaporated in vacuo to a solid

출처 및 근거

ORD 기록
ord-38950696e7234e45a9a56d5782406ba5
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06235734B1

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