Boron trifluoride etherate → HCID 12051716, compound

HRID 1019338Notes

Reaction equation

HRID 1019338 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.[CH3:24][Si:25]([CH3:39])([CH3:38])[O:26][C:27]1[CH2:32][CH2:31][CH2:30][CH2:29][C:28]=1[O:33][Si](C)(C)C.B(F)(F)F.CCOCC>ClCCl.CCOCC>[CH2:1]([N:8]1[C@@H:15]([C:27]2([O:26][Si:25]([CH3:39])([CH3:38])[CH3:24])[CH2:32][CH2:31][CH2:30][CH2:29][C:28]2=[O:33])[C@H:14]2[N:10]([C@H:11]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=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 6209801,2-bistrimethylsilyloxy cyclohexeneHCID 11450222HCID 11450222, compound

Product 1

HCID 12051716HCID 12051716, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °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 1,2-bistrimethylsilyloxy cyclohexene (0.516 parts, 2 mmol). Then the solution was cooled to 0° C. and Lewis acid for example BF3.Et2O (0.142 parts, 1 mmol) was added drop wise. The reaction mixture was stirred at 0° 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-(1-trimethylsilyloxy-2-oxocyclohexyl)-3-phenyl-(3S, 7R, 7aR)-perhydroimidazo[1,5-C][1,3]thiazole-5-one of formula (7e) (viscous liquid, 0.376 parts, 0.76 mmol) in 76% yield. And with ethyl acetate:pet.ether (25:75) as eluent provided the compound 6-benzyl-7-(1-hydroxy-2-oxocyclohexyi)-3-phenyl-(3S, 7R, 7aR)-perhydroimidazo[1,5-C][1,3]thiazole-5-one of formula (7e′) (highly viscous liquid, 0.093 parts. 0.22 mmol) in 22% 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-ebd6c8ab054643fa8ef3a1a8346247ab
Source dataset
uspto-grants-2002_11
Patent number
US06486328B1

Reaction notes

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