Potassium Carbonate → [4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]phenyl]methyl-propanedioic acid, dimethyl ester

HRID 585353

반응식

HRID 585353 반응식
Cl[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([C:19]([O:21][CH3:22])=[O:20])[C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=1)=[O:6].C(=O)([O-])[O-].[K+].[K+].[N:29]1[CH:34]=[CH:33][C:32]([C:35]([OH:48])([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:31][CH:30]=1>O.C(OCC)(=O)C.C1(C)C=CC=CC=1>[OH:48][C:35]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[CH:32]1[CH2:33][CH2:34][N:29]([CH2:2][CH2:3][CH2:4][C:5]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([C:19]([O:21][CH3:22])=[O:20])[C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=2)=[O:6])[CH2:30][CH2:31]1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 74177alpha,alpha-Diphenyl-4-pyridinemethanolHCID 86585530[4-(4-Chloro-1-oxobutyl)phenyl]methyl-propanedioic acid, dimethyl ester

생성물 1

HCID 86585531[4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]phenyl]methyl-propanedioic acid, dimethyl ester수율 76%

시약·촉매·용매 3

HCID 962Water용매2회HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

Mix together [4-(4-chloro-1-oxobutyl)phenyl]methyl-propanedioic acid, dimethyl ester (300 mg, 0.92 mmol), potassium carbonate (350 mg, 2.5 mmol), α-(4-pyridyl)benzhydrol (500 mg, 1.9 mmol), water (3 mL) and toluene (7 mL). Heat the mixture to reflux. After 5 days, cool to room temperature. Add ethyl acetate and water. Wash the organic phase with brine, dry over anhydrous magnesium sulfate and concentrate. Purify by flash chromatography (150 g of silica gel, 10% methanol/chloroform as eluent) to give the title compound (387 mg, 76%). Additionally, compounds derived from all permutations of substituents as set forth in the illustrative examples following Step F can be prepared by the synthetic procedure depicted in Step H.

후처리

  1. temperatureHeat the mixture
  2. temperatureto reflux
  3. washWash the organic phase with brine
  4. dry with materialdry over anhydrous magnesium sulfate
  5. concentrationconcentrate
  6. customPurify by flash chromatography (150 g of silica gel, 10% methanol/chloroform as eluent)

출처 및 근거

ORD 기록
ord-297d10fbe5e34e68af7ef943abe04211
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06930197B2

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