Acetic Acid → 1-(4-chlorophenethyl)-5-cyclopropyl-8-methoxy-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one

HRID 1614896노트

반응식

HRID 1614896 반응식
[CH:1]1([N:4]2[C:11](=[O:12])[CH2:10][CH2:9][NH:8][C:7]3[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:6]=3[CH2:5]2)[CH2:3][CH2:2]1.C(O)(=O)C.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH:31]=O)=[CH:26][CH:25]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClC(Cl)C>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][N:8]2[CH2:9][CH2:10][C:11](=[O:12])[N:4]([CH:1]3[CH2:2][CH2:3]3)[CH2:5][C:6]3[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:7]2=3)=[CH:26][CH:25]=1

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 114125022-(4-Chlorophenyl)acetaldehydeHCID 529398795-cyclopropyl-8-methoxy-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one

생성물 1

HCID 529398801-(4-chlorophenethyl)-5-cyclopropyl-8-methoxy-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one수율 76%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

To a solution of 5-cyclopropyl-8-methoxy-2,3,5,6-tetrahydrobenzo[b][1,5]diazocin-4(1H)-one (50.0 mg, 0.203 mmol) from Example 1 in dichloroethane (2 ml) at 0° C. was added acetic acid (0.035 ml, 0.609 mmol), 2-(4-chlorophenyl)acetaldehyde (47.0 mg, 0.304 mmol) prepared as above and sodium triacetoxyborohydride (129.0 mg, 0.609 mmol). The mixture was stirred overnight at room temperature and then sodium bicarbonate was added followed by extraction with dichloromethane. The organic phases were dried over sodium sulfate, filtered and concentrated. Preparative thin layer chromatography (pentane/ethyl acetate: 1/1) of the obtained residue gave the desired compound as a yellow oil (59 mg, 76%).

후처리

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe organic phases were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-01ffbf3cc2d84144840891b10a37a4b0
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765728B2

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