Acetic Acid → HCID 58531372, 화합물

HRID 1889688노트

반응식

HRID 1889688 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH2:9])=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]=O)[CH:18]=2)=[CH:13][CH:12]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][NH:9][CH2:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH:18]=2)=[CH:15][CH:16]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 673264-Fluorobenzylamine2회HCID 13942383-(4-Chlorophenyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 58531372HCID 58531372, 화합물수율 62.7%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

To a homogeneous mixture of (4-fluorophenyl)methanamine (2.5 mL, 21.8 mmol) and 4′-chlorobiphenyl-3-carbaldehyde (Aldrich, 3.6 g, 16.8 mmol) in anhydrous dichloroethane (25 mL), under nitrogen atmosphere, was added acetic acid (1.2 mL, 21.0 mmol). The mixture was stirred at room temperature for 13.5 h before sodium triacetoxyborohydride (5.0 g, 23.5 mmol) was added. After 4 h, (4-fluorophenyl)methanamine (2.5 mL, 21.8 mmol) was added and the stirring continued. After an additional 5 h of stirring, the reaction was quenched with 1 N aq. NaOH solution (50 mL) then extracted twice with chloroform. The organic extracts were combined, washed with saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel flash chromatography (Merck KGaA, 230-400 mesh particle size) eluting with 0-70% ethyl acetate in hexane, to afford the title compound (3.43 g, 59%) as a colorless oil. MS (ESI): 326.1 (M+H)+.

후처리

  1. additionwas added
  2. customthe reaction was quenched with 1 N aq. NaOH solution (50 mL)
  3. extractionthen extracted twice with chloroform
  4. washwashed with saturated aqueous NaHCO3 and brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel flash chromatography (Merck KGaA, 230-400 mesh particle size)
  9. washeluting with 0-70% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-0b7c915ef6c34d6ca8929ef09376ce51
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501992B2

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