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 522220Notes

Reaction equation

HRID 522220 reaction equation
[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

Participants

5

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 11147261(1,3-Dimesitylimidazolidin-2-ylidene)(tricyclohexylphosphine)benzylidene ruthenium dichlorideCatalystHCID 7962MethylcyclohexaneSolvent

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-4eb3b16da39049bb9d025d1ac48bcd79
Source dataset
uspto-grants-2016_05
Patent number
US09328112B2

Reaction notes

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