Boron trifluoride etherate → HCID 11337066, compound

HRID 1019340Notes

Reaction equation

HRID 1019340 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.[CH2:24]([Si](C)(C)C)[CH:25]=[CH2:26].B(F)(F)F.CCOCC>ClCCl.CCOCC>[CH2:26]([C@H:15]1[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](=[O:23])[N:8]1[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:25]=[CH2:24]

Participants

6

Reactant 3

HCID 8000Boron trifluoride etherateHCID 69808AllyltrimethylsilaneHCID 11450222HCID 11450222, compound

Product 1

HCID 11337066HCID 11337066, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

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 allyltrimethylsilane (0.228 parts, 2 mmol). Then Lewis acid for example BF3.Et2O (0.142 parts, 1 mmol) was added drop wise to reaction mixture at 30° C. was stirred for 30 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 7-allyl-6-benzyl-3-phenyl-(3S, 7S, 7aR)-perhydroimidazo[1,5-C][1,3]thiazol-5-one of formula (7f) (viscous liquid, 0.343 parts, 0.98 mmol) in 98% yield.

Workup

  1. customwise to reaction mixture at 30° C.
  2. customand the reaction mixture was quenched with saturated ammonium chloride (10 parts)
  3. customThen the organic layer was separated
  4. concentrationconcentrated
  5. customcolumn purification with ethylacetate

Sources & evidence

ORD record
ord-aad9fe99cbdf4ef3862f17eb07515342
Source dataset
uspto-grants-2002_11
Patent number
US06486328B1

Reaction notes

Loading…