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Cyanomethylenetributylphosphorane → Benzyl 9a-methyl-3-((S)-3-methyl-1-oxoisochroman-6-yl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

HRID 2175786
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인쇄 미리보기

반응식

HRID 2175786 반응식
O[CH:2]([C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[C:29](=[O:33])[O:28][C@@H:27]([CH3:34])[CH2:26]2)[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6][C:5]1([CH2:21][OH:22])[CH3:20].C(C=P(CCCC)(CCCC)CCCC)#N>C1C=CC=CC=1>[CH3:20][C:5]12[CH2:6][N:7]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:11])[CH2:8][CH2:9][N:4]1[CH2:3][CH:2]([C:23]1[CH:24]=[C:25]3[C:30](=[CH:31][CH:32]=1)[C:29](=[O:33])[O:28][C@@H:27]([CH3:34])[CH2:26]3)[O:22][CH2:21]2
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참가 물질

4

반응물 2

HCID 4622928CyanomethylenetributylphosphoraneHCID 86727035benzyl 4-(2-hydroxy-2-((S)-3-methyl-1-oxoisochroman-6-yl)ethyl)-3-(hydroxymethyl)-3-methylpiperazine-1-carboxylate

생성물 1

HCID 86727034Benzyl 9a-methyl-3-((S)-3-methyl-1-oxoisochroman-6-yl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

시약·촉매·용매 1

HCID 241Benzene용매

반응 조건

온도
135 °C

실험 절차

The mixture of benzyl 4-(2-hydroxy-2-((S)-3-methyl-1-oxoisochroman-6-yl)ethyl)-3-(hydroxymethyl)-3-methylpiperazine-1-carboxylate (762 mg, 1.60 mmol) and cyanomethylenetributylphosphorane (471 mg, 1.90 mmol) in dry benzene was degassed and heated to 135° C. in a microwave reactor for 3.5 h. After which point, the reaction mixture was cooled down to rt, concentrated to dryness and purified on silica gel to afford the title compound (cis or trans): MS: m/e 451.2 (M+H)+.

후처리

  1. customwas degassed
  2. temperatureAfter which point, the reaction mixture was cooled down to rt
  3. concentrationconcentrated to dryness
  4. custompurified on silica gel

출처 및 근거

ORD 기록
ord-b049ce2e143a4fde907573ba5585dd99
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09062070B2

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