Dimethyl malonate → HCID 10377066, 화합물

HRID 916303

반응식

HRID 916303 반응식
[C:1]1(=[O:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[C:9]([O:16][CH3:17])(=[O:15])[CH2:10][C:11]([O:13][CH3:14])=[O:12]>CC(O)(C)C>[CH3:14][O:13][C:11]([CH:10]([C:9]([O:16][CH3:17])=[O:15])[C@@H:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C:1](=[O:8])[CH2:2]1)=[O:12]

참가 물질

4

반응물 2

HCID 7943Dimethyl malonateHCID 707232-Cyclohepten-1-one

생성물 1

HCID 10377066HCID 10377066, 화합물수율 75%

시약·촉매·용매 1

HCID 6386tert-Butanol용매

반응 조건

온도
30 °C

실험 절차

Under an atmosphere of argon, 11.0 mg (0.02 mmol, S/C=100) of Ru[(S,S)-Msdpen] (hexamethylbenzene), 111 μL (1.0 mmol) of 2-cycloheptenone, 114 μL (1.0 mmol) of dimethyl malonate, and 1 mL of 2-methyl-2-propanol were placed in a 20 mL Schlenk tube and stirred at 30° C. for 72 hours. This solution was purified by flash column chromatography (hexane/acetone=90/10, SiO2) to give 181 mg (75% yield) of the title compound. The optical rotation [α]D27 was +45.2 (c 1.76, CHCl3). This was reacted with (2R,3R)-butanediol in the presence of a catalytic amount of p-toluenesulfonic acid so as to be converted into a ketal derivative. The 13C NMR spectrum of this derivative was measured, and the optical purity was determined from the ratio of the integrals of the peaks of two diastereomers, with the result that it was >99% ee.

후처리

  1. customThis solution was purified by flash column chromatography (hexane/acetone=90/10, SiO2)

출처 및 근거

ORD 기록
ord-3c1b66f40c8c47fcb221ac9605d038ef
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07268250B2

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