Cyanomethylenetributylphosphorane → tert-butyl(9aS)-3-(3-cyano-2,4-difluorophenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

HRID 1502013노트

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HRID 1502013 반응식
[C:1]([C:3]1[C:4]([F:28])=[C:5]([CH:10](O)[CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][C@H:13]2[CH2:25][OH:26])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].C(C=P(CCCC)(CCCC)CCCC)#N>C1C=CC=CC=1>[C:1]([C:3]1[C:4]([F:28])=[C:5]([CH:10]2[O:26][CH2:25][C@@H:13]3[CH2:14][N:15]([C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[CH2:16][CH2:17][N:12]3[CH2:11]2)[CH:6]=[CH:7][C:8]=1[F:9])#[N:2]

참가 물질

4

반응물 2

HCID 4622928CyanomethylenetributylphosphoraneHCID 86727062HCID 86727062, 화합물

생성물 1

HCID 86727063tert-butyl(9aS)-3-(3-cyano-2,4-difluorophenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

시약·촉매·용매 1

HCID 241Benzene용매

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온도
100 °C

실험 절차

tert-Butyl (3S)-4-[2-(3-cyano-2,4-difluorophenyl)-2-hydroxyethyl]-3-(hydroxymethyl)piperazine-1-carboxylate (1.2 g, 3.0 mmol) and cyanomethylenetri-n-butylphosphorane (1.31 g, 5.44 mmol) were dissolved in 5 mL of benzene. The reaction mixture was degassed and heated to 100° C. for 16 h. LC-MS analysis showed product peak at 2.07 min (M+1=380). The reaction was cooled and evaporated to dryness. The residue was purified by MPLC chromatography through an 80 g Redi-sep column eluting with a 40% EtOAc/60% hexane mixture to yield a cis-trans mixture of the title compound.

후처리

  1. customThe reaction mixture was degassed
  2. customat 2.07 min
  3. temperatureThe reaction was cooled
  4. customevaporated to dryness
  5. customThe residue was purified by MPLC chromatography through an 80 g Redi-sep column
  6. washeluting with a 40% EtOAc/60% hexane mixture
  7. customto yield

출처 및 근거

ORD 기록
ord-7696e789dbb14713928cc7d2a5e9f623
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206199B2

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