1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-Vinyl-morpholine-2,4-dicarboxylic acid 4-tert-butyl ester 2-methyl ester

HRID 2176238노트

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HRID 2176238 반응식
[CH3:1][O:2][C:3]([C:5]1([CH:18](OS(C(F)(F)F)(=O)=O)[CH3:19])[O:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]1)=[O:4].N12CCCN=C1CCCCC2>ClCCl>[CH3:1][O:2][C:3]([C:5]1([CH:18]=[CH2:19])[O:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])[CH2:6]1)=[O:4]

참가 물질

4

반응물 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 867060772-(1-Trifluoromethanesulfonyloxy-ethyl)-morpholine-2,4-dicarboxylic acid 4-tert-butyl ester 2-methyl ester

생성물 1

HCID 867060762-Vinyl-morpholine-2,4-dicarboxylic acid 4-tert-butyl ester 2-methyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
35 °C

실험 절차

A warm (35° C.) solution of 2-(1-trifluoromethanesulfonyloxy-ethyl)-morpholine-2,4-dicarboxylic acid 4-tert-butyl ester 2-methyl ester (1.384 g, 3.284 mmol) in dichloromethane (40 mL) was treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (2.5 mL, 16.422 mmol). After stirring at 35° C. for 2 h, the reaction was cooled to 0° C. and quenched with hydrochloric acid (1 M, 50 mL). The aqueous layer was extracted with dichloromethane. The organics were combined, filtered through a phase separator and the volatiles were removed in vacuo to provide the title compound as an orange oil which was used without further purification in the next step. 1H NMR (300 MHz, CDCl3) δ 1.49 (s, 9H), 3.13-3.29 (m, 2H), 3.60-3.73 (m, 1H), 3.79 (s, 3H), 3.83-3.92 (m, 2H), 4.24 (d, J=13.1 Hz, 1H), 5.37 (d, J=10.9 Hz, 1H), 5.55 (d, J=17.4 Hz, 1H), 5.84 (dd, J=17.4, 10.9 Hz, 1H).

후처리

  1. temperaturethe reaction was cooled to 0° C.
  2. customquenched with hydrochloric acid (1 M, 50 mL)
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. filtrationfiltered through a phase separator
  5. customthe volatiles were removed in vacuo

출처 및 근거

ORD 기록
ord-3250a752892644fa9120e88b66c1270c
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062092B2

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