Triethylamine → (1RS,2SR,6RS,7SR)-4-(3,5-dimethylbiphenyl-4-yl)-5-oxo-10-oxa-tricyclo[5.2.1.02,6]dec-3-en-3-yl 2,2-dimethylpropionate

HRID 1430767노트

반응식

HRID 1430767 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:5]=[C:6]([CH3:20])[C:7]=1[CH:8]1[C:16](=[O:17])[CH:15]2[CH:10]([CH:11]3[O:18][CH:14]2[CH2:13][CH2:12]3)[C:9]1=[O:19].C(N(CC)CC)C.[C:34](Cl)(=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36]>ClCCl>[CH3:36][C:35]([CH3:38])([CH3:37])[C:34]([O:19][C:9]1[CH:10]2[CH:15]([C:16](=[O:17])[C:8]=1[C:7]1[C:2]([CH3:1])=[CH:3][C:4]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:5][C:6]=1[CH3:20])[CH:14]1[O:18][CH:11]2[CH2:12][CH2:13]1)=[O:39]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 67777251(1RS,2SR,6RS,7SR)-4-(3,5-dimethylbiphen-4-yl)-10-oxa-tricyclo[5.2.1.02,6]decane-3,5-dione

생성물 1

HCID 67777293(1RS,2SR,6RS,7SR)-4-(3,5-dimethylbiphenyl-4-yl)-5-oxo-10-oxa-tricyclo[5.2.1.02,6]dec-3-en-3-yl 2,2-dimethylpropionate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (1RS,2SR,6RS,7SR)-4-(3,5-dimethylbiphenyl-4-yl)-10-oxa-tricyclo-[5.2.1.02,6]decane-3,5-dione (80 mg, 0.23 mmol) in dichloromethane (5 ml) and triethylamine (140 μl, 1 mmol) is added pivaloyl chloride (124 μl, 1 mmol) at room temperature. The reaction mixture is stirred overnight at room temperature. Silica gel is added to the crude reaction mixture, the solvent is evaporated under reduced pressure and the residue is purified by column chromatography on silica gel to give (1RS,2SR,6RS,7SR)-4-(3,5-dimethylbiphenyl-4-yl)-5-oxo-10-oxa-tricyclo[5.2.1.02,6]dec-3-en-3-yl 2,2-dimethylpropionate.

후처리

  1. additionSilica gel is added to the crude
  2. customreaction mixture
  3. customthe solvent is evaporated under reduced pressure
  4. customthe residue is purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-41fd8b736d794217b5729eab761df3c9
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940913B2

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