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

HRID 2176238ノート

反応式

HRID 2176238 の反応式
[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]

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
35 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3250a752892644fa9120e88b66c1270c
出典データセット
uspto-grants-2015_06
特許番号
US09062092B2

反応ノート

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