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

HRID 470214노트

반응식

HRID 470214 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-37a76f4736a445e5b2ea4328c7ac15c0
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629270B2

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