Acetic Acid → HCID 59264602, 화합물

HRID 646201노트

반응식

HRID 646201 반응식
[CH3:1][C:2]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)([CH3:7])[C:3]([O:5][CH3:6])=[O:4].[F:15][C:16]([F:32])([F:31])[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][C:26]([CH2:29][NH2:30])=[CH:25][CH:24]=2)=[CH:19][CH:18]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>ClCCCl>[CH3:1][C:2]([N:8]1[CH2:13][CH2:12][CH:11]([NH:30][CH2:29][C:26]2[CH:25]=[CH:24][C:23]([C:20]3[CH:21]=[CH:22][C:17]([C:16]([F:15])([F:31])[F:32])=[CH:18][CH:19]=3)=[CH:28][CH:27]=2)[CH2:10][CH2:9]1)([CH3:7])[C:3]([O:5][CH3:6])=[O:4]

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 37291554-(4-TRIFLUOROMETHYLPHENYL)BENZYLAMINEHCID 5049666Sodium triacetoxyborohydrideHCID 59264606HCID 59264606, 화합물

생성물 1

HCID 59264602HCID 59264602, 화합물수율 67.1%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

A mixture of methyl 2-methyl-2-(4-oxo-1-piperidinyl)propanoate (Int. A3) (14.28 g, 1 equiv), {[4′-(trifluoromethyl)-4-biphenylyl]methyl}amine (Int. A1) (19.6 g, 0.85 equiv), DCE (300 ml), acetic acid (3.8 ml, 0.90 equiv) and sodium triacetoxyborohydride (20.7 g, 1.25 equiv) was stirred at room temperature under nitrogen for 17.5 h. Aqueous sodium carbonate (2M solution, excess) was added and stirred for 4 h, then the mixture was extracted with a mixture of diethyl ether and THF. The organic extracts were backwashed with water and brine, dried over sodium sulfate and filtered through a pad of silica gel which was rinsed with 2.5% methanol in DCM. After evaporation in vacuo, the crude product was crystallised from ether/hexane, finally at ice bath temperature, which after drying yielded a white solid (20.9 g).

후처리

  1. stirringstirred for 4 h
  2. extractionthe mixture was extracted with a mixture of diethyl ether and THF
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered through a pad of silica gel which
  5. washwas rinsed with 2.5% methanol in DCM
  6. customAfter evaporation in vacuo
  7. customthe crude product was crystallised from ether/hexane, finally at ice bath temperature, which
  8. customafter drying

출처 및 근거

ORD 기록
ord-4434b58834e54435aefa603c1db686ac
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705005B2

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