Diethyl Ether → HCID 57827731, compound

HRID 1842154Notes

Reaction equation

HRID 1842154 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]12[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]1[CH2:13][S:12][C:11]([NH2:19])=[N:10]2.[Br:20]N1C(=O)CCC1=O.CCOCC.C(=O)(O)[O-].[Na+]>S(=O)(=O)(O)O>[Br:20][C:5]1[C:6]([F:8])=[CH:7][C:2]([F:1])=[C:3]([C@:9]23[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]2[CH2:13][S:12][C:11]([NH2:19])=[N:10]3)[CH:4]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 57827646HCID 57827646, compound

Product 1

HCID 57827731HCID 57827731, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

(±)-(4aR*,8aS*)-8a-(2,4-Difluoro-phenyl)-4a,5,6,7,8,8a-hexahydro-4H-benzo[d][1,3]thiazin-2-ylamine (270 mg) was dissolved in concentrated sulfuric acid (3 mL). N-Bromosuccinimide (170 mg) was added in an ice bath, and the mixture was stirred at the same temperature for two hours. Ice was added to terminate the reaction, followed by dilution with ether. The reaction solution was neutralized with a sodium bicarbonate solution, and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (330 mg).

Workup

  1. additionIce was added
  2. customto terminate
  3. customthe reaction
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fe9a34bb044040668f138d034cc3a990
Source dataset
uspto-grants-2015_02
Patent number
US08946211B2

Reaction notes

Loading…