Cesium carbonate → tert-Butyl 1-oxo-2-(5-oxo-2,5-dihydrofuran-3-yl)-2,9-diazaspiro[5.5]undecane-9-carboxylate

HRID 1848444노트

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HRID 1848444 반응식
[O:1]=[C:2]1[C:7]2([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][NH:3]1.Br[C:21]1[CH2:25][O:24][C:23](=[O:26])[CH:22]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:1]=[C:2]1[C:7]2([CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:12]2)[CH2:6][CH2:5][CH2:4][N:3]1[C:21]1[CH2:25][O:24][C:23](=[O:26])[CH:22]=1

참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 117895364-bromo-5H-furan-2-oneHCID 49760149tert-Butyl 1-oxo-2,9-diazaspiro[5.5]undecane-9-carboxylate

생성물 1

HCID 86709452tert-Butyl 1-oxo-2-(5-oxo-2,5-dihydrofuran-3-yl)-2,9-diazaspiro[5.5]undecane-9-carboxylate

시약·촉매·용매 1

HCID 9811564Bis(dibenzylideneacetone)palladium촉매

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온도
90 °C

실험 절차

A microwave vial was charged with commercially available tert-butyl 1-oxo-2,9-diazaspiro[5.5]undecane-9-carboxylate (Shanghai AQ BioPharma Co., Ltd, catalog #ABP3640, 100 mg, 0.373 mmol), 4-bromofuran-2(5H)-one (72.9 mg, 0.447 mmol), Pd2(dba)3 (17.06 mg, 0.019 mmol), Xantphos (32.3 mg, 0.056 mmol), and cesium carbonate (182 mg, 0.559 mmol). The vial was sealed, degassed, and filled with toluene (1.5 mL). The reaction mixture was heated at 90° C. overnight, and was filtered through CELITE®. The filtrate was evaporated to give the crude product, which was purified by column chromatograph (0-10% MeOH/DCM) to afford the title compound. LC/MS: [(M+1-56)]+=295

후처리

  1. customThe vial was sealed
  2. customdegassed
  3. additionfilled with toluene (1.5 mL)
  4. filtrationwas filtered through CELITE®
  5. customThe filtrate was evaporated
  6. customto give the crude product, which
  7. customwas purified by column chromatograph (0-10% MeOH/DCM)

출처 및 근거

ORD 기록
ord-9159bd42539d458595b3ea9338674399
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952166B2

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