Sodium borohydride → HCID 22728863, compound

HRID 2085014Notes

Reaction equation

HRID 2085014 reaction equation
Cl.[O:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5](N)[CH2:4][CH2:3]1.[F:13][C:14]([F:26])([F:25])[C:15]([N:17]1[CH2:22][CH2:21][C:20](=O)[CH:19]([CH3:24])[CH2:18]1)=[O:16].[BH4-].[Na+]>CC(O)C>[F:26][C:14]([F:13])([F:25])[C:15]([N:17]1[CH2:22][CH2:21][CH:20]2[N:5]3[CH2:4][CH2:3][O:2][C:7]4[CH:8]=[CH:9][CH:10]=[C:11]([C:6]3=4)[C:19]2([CH3:24])[CH2:18]1)=[O:16]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 224889852H-benzo[b][1,4]oxazin-4(3H)-amine hydrochlorideHCID 227288623-Methyl-1-(trifluoroacetyl)piperidin-4-one

Product 1

HCID 22728863HCID 22728863, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2,3-Dihydro-4H-1,4-benzoxazin-4-amine hydrochloride (0.0830 g, 0.444 mmol) and 1-trifluoroacetyl-3-methylpiperidin-4-one (0.0929 g, 0.444 mmol) were combined in 2-propanol (3.75 mL) and stirred at reflux for 3.75 hours under N2. The reaction mixture was cooled to room temperature, NaBH4 (0.0523 g, 1.38 mmol) was added and the reaction mixture was refluxed for 1 hour under N2. The cooled reaction mixture was quenched with CH3OH (2 mL) and partitioned between CH2Cl2 and H2O. The layers were separated and the aqueous layer was extracted with CH2Cl2. The combined CH2Cl2 extracts were washed with H2O, dried over Na2SO4, filtered and concentrated to yield crude 8-trifluoroacetyl-6b-methyl-1,2,6b,7,8,9,10,10a-octahydro[1,4]oxazino[2,3,4-hi]pyrido[4,3-b]indole (0.130 g). MS (ESI+) for C16H17F3N2O2 m/z 327.0 (M+H)+.

Workup

  1. temperatureat reflux for 3.75 hours under N2
  2. temperaturethe reaction mixture was refluxed for 1 hour under N2
  3. customThe cooled reaction mixture
  4. customwas quenched with CH3OH (2 mL)
  5. custompartitioned between CH2Cl2 and H2O
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with CH2Cl2
  8. washThe combined CH2Cl2 extracts were washed with H2O
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-2cae8eb583364112a74622ab3318f9a8
Source dataset
uspto-grants-2004_04
Patent number
US06720316B2

Reaction notes

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