Diethyl Ether → (+/-)-(4aR*,8aS*)-8a-(3-nitrophenyl)-4a,5,6,7,8,8a-hexahydro-4H-benzo[d][1,3]thiazin-2-ylamine

HRID 1693154Notes

Reaction equation

HRID 1693154 reaction equation
FC(F)(F)S(O)(=O)=O.Cl.[N+:10]([C:13]1[CH:14]=[C:15]([C:19]2[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=2[CH2:25][S:26][C:27](=[NH:29])[NH2:28])[CH:16]=[CH:17][CH:18]=1)([O-:12])=[O:11].C(=O)(O)[O-].[Na+].CCOCC>C(O)(C(F)(F)F)=O>[N+:10]([C:13]1[CH:14]=[C:15]([C@:19]23[CH2:24][CH2:23][CH2:22][CH2:21][C@H:20]2[CH2:25][S:26][C:27]([NH2:28])=[N:29]3)[CH:16]=[CH:17][CH:18]=1)([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 62406Trifluoromethanesulfonic acid2×HCID 516892Sodium BicarbonateHCID 672787672-[2-(3-Nitrophenyl)cyclohex-1-enylmethyl]isothiourea hydrochloride

Product 1

HCID 59621307(+/-)-(4aR*,8aS*)-8a-(3-nitrophenyl)-4a,5,6,7,8,8a-hexahydro-4H-benzo[d][1,3]thiazin-2-ylamine

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Trifluoromethanesulfonic acid (1.00 mL) was added to a solution of 2-[2-(3-nitrophenyl)cyclohex-1-enylmethyl]isothiourea hydrochloride obtained in Preparation Example 4-(4) (2.04 g) in TFA (10.0 mL) in an ice bath. The reaction solution was warmed to room temperature, followed by stirring overnight. Trifluoromethanesulfonic acid (1.00 mL) was further added to the reaction solution, followed by stirring for two days. After confirming completion of the reaction, the reaction mixture was carefully poured into a mixed solution of a saturated sodium bicarbonate solution and ether in an ice bath. The aqueous layer was extracted with ethyl acetate, and the organic layer was washed with a saturated sodium bicarbonate solution and a saturated sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure to obtain a crude product. The resulting crude product was purified by NH-silica gel column chromatography to obtain the title compound (1.62 g).

Workup

  1. stirringby stirring for two days
  2. customcompletion of the reaction
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe organic layer was washed with a saturated sodium bicarbonate solution
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customThe drying agent was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customto obtain a crude product
  9. customThe resulting crude product was purified by NH-silica gel column chromatography

Sources & evidence

ORD record
ord-cb552f84e50f445ca0665316fe242749
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

Loading…