Boron trifluoride etherate → HCID 11188970, compound

HRID 1019337Notes

Reaction equation

HRID 1019337 reaction equation
[CH2:1]([N:8]1[CH:15](O)[C@H:14]2[N:10]([C@H:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[S:12][CH2:13]2)[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](C)(C)[O:26][C:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]=1.B(F)(F)F.CCOCC>ClCCl.CCOCC>[CH2:1]([N:8]1[C@@H:15]([CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32][C:27]2=[O:26])[C@H:14]2[N:10]([C@H:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[S:12][CH2:13]2)[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8000Boron trifluoride etherateHCID 81161Cyclohexene, 1-((trimethylsilyl)oxy)-HCID 11450222HCID 11450222, compound

Product 1

HCID 11188970HCID 11188970, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of compound 6-benzyl-7-hydroxy-3-phenyl-(3S, 7aR)-perhydroimidazo[1,5-C][1,3]thiazol-5-one of formula (6) (0.326 parts, 1 mmol) in dichloromethane (10 parts) was added 1-trimethylsilyloxy-1-cyclohexene (0.340 parts. 2 mmol). Then the solution was cooled to 20° C., and Lewis acid for example BF3.Et2O (0.142 parts, 1 mmol) was added drop wise. The reaction mixture was stirred at 20° C. for 10 mints. and the reaction mixture was quenched with saturated ammonium chloride (10 parts). Then the organic layer was separated, concentrated and column purification with ethylacetate:pet.ether (15:85) as eluent provided compound 6-benzyl-7-(2-oxocyclohexyl)-3-phenyl-(3S, 7S, 7aR)-perhydroimidazo[1,5-C][1,3]-thiazol-5-one of formula (7d) (viscous liquid, 0.398 parts, 0.98 mmol) in98% yield.

Workup

  1. customand the reaction mixture was quenched with saturated ammonium chloride (10 parts)
  2. customThen the organic layer was separated
  3. concentrationconcentrated
  4. customcolumn purification with ethylacetate

Sources & evidence

ORD record
ord-05a912cc1fc343888625c8ecbab71cc2
Source dataset
uspto-grants-2002_11
Patent number
US06486328B1

Reaction notes

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