Boron trifluoride → Benzyl 6a-phenyl-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5-carboxylate

HRID 470214ノート

反応式

HRID 470214 の反応式
B(F)(F)F.[N:5]1[O:6][CH2:7][CH:8]2[CH2:12][N:11]([C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])[CH2:10][C:9]=12.[C:23]1([Mg]Br)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1>[C:23]1([C:9]23[CH2:10][N:11]([C:13]([O:15][CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[O:14])[CH2:12][CH:8]2[CH2:7][O:6][NH:5]3)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

5

反応物 3

HCID 6356Boron trifluorideHCID 86697896Benzyl 3a,4-dihydro-3H-pyrrolo[3,4-c]isoxazole-5(6H)-carboxylateHCID 178418255HCID 178418255、化合物

生成物 1

HCID 86697899Benzyl 6a-phenyl-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5-carboxylate収率 59%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Boron trifluoride (30.8 mL, 244 mmol) is added to a −50° C. solution of benzyl 3,3a,4,6-tetrahydropyrrolo[3,4-c]isoxazole-5-carboxylate (40 g, 162 mmol) in tetrahydrofuran (200 mL). The mixture is stirred for 10 minutes and the solution is added to phenyl magnesium bromide (325 mL, 325 mmol, 1 M in tetrahydrofuran) at −50° C., warmed to 0° C., and stirred for 4 hours. The reaction is quenched with saturated ammonium chloride (200 mL) and the aqueous layer is separated. The organic layer is dried over magnesium sulfate and the solvent is removed under vacuum. The crude product is purified over silica gel using a 5 to 50% ethyl acetate/hexanes gradient to give the title compound (31 g, 59%). ES/MS (m/e): 325 (M+H).

後処理

  1. stirringstirred for 4 hours
  2. customThe reaction is quenched with saturated ammonium chloride (200 mL)
  3. customthe aqueous layer is separated
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. customthe solvent is removed under vacuum
  6. customThe crude product is purified over silica gel using a 5 to 50% ethyl acetate/hexanes gradient

出典と根拠

ORDレコード
ord-37a76f4736a445e5b2ea4328c7ac15c0
出典データセット
uspto-grants-2014_01
特許番号
US08629270B2

反応ノート

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