Diethylene glycol vinyl ether → tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3,6,7-tetrahydro-1H-azepine-1-carboxylate

HRID 522220

반응식

HRID 522220 반응식
[CH2:1]([N:5]([CH2:13][CH2:14][C:15]([B:17]1[O:21][C:20]([CH3:23])([CH3:22])[C:19]([CH3:25])([CH3:24])[O:18]1)=[CH2:16])[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH2:2]C=C.C(OCCOCCO)=C>CC1CCCCC1.CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C=CC=CC=3)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1>[CH3:23][C:20]1([CH3:22])[C:19]([CH3:25])([CH3:24])[O:18][B:17]([C:15]2[CH2:14][CH2:13][N:5]([C:6]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:12])[CH2:1][CH2:2][CH:16]=2)[O:21]1

참가 물질

5

반응물 2

HCID 13581Diethylene glycol vinyl etherHCID 131735521Tert-butyl but-3-en-1-yl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-1-yl)carbamate

생성물 1

HCID 68054971tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3,6,7-tetrahydro-1H-azepine-1-carboxylate

시약·촉매·용매 2

HCID 11147261(1,3-Dimesitylimidazolidin-2-ylidene)(tricyclohexylphosphine)benzylidene ruthenium dichloride촉매HCID 7962Methylcyclohexane용매

실험 절차

A solution of Example 87B (7.28 g, 20.72 mmol) in methyl cyclohexane (1.5 L) was degassed with nitrogen and (1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium (250 mg, 0.294 mmol) was added. The mixture was stirred at room temperature overnight and diethyleneglycol vinyl ether (0.16 mL) was added to inactivate any remaining active catalyst. The mixture was stirred for 30 minutes, concentrated and purified by flash chromatography on silica using an Analogix system (0-10% ethyl acetate/heptane) to provide the title compound. MS (ESI+) m/z 346 (M+Na)+.

후처리

  1. additionwas added
  2. stirringThe mixture was stirred for 30 minutes
  3. concentrationconcentrated
  4. custompurified by flash chromatography on silica using an Analogix system (0-10% ethyl acetate/heptane)

출처 및 근거

ORD 기록
ord-4eb3b16da39049bb9d025d1ac48bcd79
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328112B2

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