Sodium triacetoxyborohydride → HCID 71112545, 화합물

HRID 1472757노트

반응식

HRID 1472757 반응식
[OH:1][C:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:3]([O:5][CH2:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)=[O:4].[O:25]1[CH2:29][CH2:28][O:27][CH:26]1[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:35][C:36]1[CH:43]=[CH:42][C:39]([CH:40]=O)=[CH:38][CH:37]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[OH:1][C:2]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:3]([O:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([CH2:40][C:39]2[CH:38]=[CH:37][C:36]([O:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH:26]3[O:25][CH2:29][CH2:28][O:27]3)=[CH:43][CH:42]=2)[CH2:9][CH2:8]1)=[O:4]

참가 물질

5

반응물 3

HCID 5049666Sodium triacetoxyborohydrideHCID 71093464HCID 71093464, 화합물HCID 86676461HCID 86676461, 화합물

생성물 1

HCID 71112545HCID 71112545, 화합물수율 70.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of piperidin-4-ylmethyl 2-hydroxy-2,2-diphenylacetate (0.4 g, 1.23 mmol) and 4-((5-(1,3-dioxolan-2-yl)pentyl)oxy)benzaldehyde (0.38 g, 1.44 mmol) in DCM (5 mL) was added sodium triacetoxyborohydride (0.388 g, 1.83 mmol). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was partitioned between EtOAc and saturated sodium hydrogen carbonate. The organic phase was dried (sodium sulfate), filtered, and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography eluting with 1 to 10% methanol in ethyl acetate to afford the title compound as a colourless oil (0.50 g, 26%).

후처리

  1. customThe reaction mixture was partitioned between EtOAc and saturated sodium hydrogen carbonate
  2. dry with materialThe organic phase was dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified by silica gel column chromatography
  6. washeluting with 1 to 10% methanol in ethyl acetate

출처 및 근거

ORD 기록
ord-fdff5b2b358b44d0a060dcbea15e4be6
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012644B2

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