Potassium Carbonate → HCID 18416130, compound

HRID 1350168Notes

Reaction equation

HRID 1350168 reaction equation
O[C:2]1([C:20]([F:23])([F:22])[F:21])[N:7]([CH2:8][C:9]([F:12])([F:11])[F:10])[C:6]2[CH:13]=[CH:14][C:15]([N+:17]([O-:19])=[O:18])=[CH:16][C:5]=2[O:4][CH2:3]1.C([BH3-])#N.[Na+].C(=O)([O-])[O-].[K+].[K+]>FC(F)(F)C(O)=O.O>[N+:17]([C:15]1[CH:14]=[CH:13][C:6]2[N:7]([CH2:8][C:9]([F:12])([F:11])[F:10])[CH:2]([C:20]([F:21])([F:22])[F:23])[CH2:3][O:4][C:5]=2[CH:16]=1)([O-:19])=[O:18]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 21094347HCID 21094347, compound

Product 1

HCID 18416130HCID 18416130, compoundYield 53.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of (±)-3,4-dihydro-3-hydroxy-7-nitro-4-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)-2H-1,4-benzoxazine (0.10 g, 0.29 mmol) in 3 mL of trifluoroacetic acid and then sodium cyanoborohydride (3.0 g, 47.4 rmmol) was slowly added via an solid addition funnel under nitrogen at 0° C. over the course of 30 minutes the reaction was allowed to warm to rt and stirred for 12 hours. The reaction mixture was then diluted with water and cooled to 0° C. Solid potassium carbonate was then added slowly to pH 7.The solution was extracted with ethyl acetate (2×100 mL) and the combined organic layers were washed with brine (50 mL), dried over magnesium sulfate, filtered and evaporated under reduced pressure to give an oil. The oil was purified via flash chromatography (7:3 hexanes:EtOAc) to afford 51 mg (52%) of (±)-3,4-dihydro-7-nitro-4-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)-2H-1,4-benzoxazine. 1H NMR (400 MHz, CDCl3) d 7.87 (dd, 1H, J=9.1, 2.8), 7.81 (d, 1H, J=2.5), 6.92 (d, 1H, J=9.1), 4.73 (d, 1H, J=12.1), 4.48–4.39 (m, 1H), 4.13–4.06 (m, 2H), 3.99–3.88 (mn, 1H).

Workup

  1. temperaturecooled to 0° C
  2. extractionThe solution was extracted with ethyl acetate (2×100 mL)
  3. washthe combined organic layers were washed with brine (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto give an oil
  8. customThe oil was purified via flash chromatography (7:3 hexanes:EtOAc)

Sources & evidence

ORD record
ord-39cc6cb09d48462f80fc062843c980e1
Source dataset
uspto-grants-2007_05
Patent number
US07214690B2

Reaction notes

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