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

HRID 2175838ノート

反応式

HRID 2175838 の反応式
[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]

参加物

4

反応物 2

HCID 4622928CyanomethylenetributylphosphoraneHCID 86727062HCID 86727062、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-176cf856438743debc7edd745ef6a6b8
出典データセット
uspto-grants-2015_06
特許番号
US09062070B2

反応ノート

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