Sodium borohydride → HCID 58641516, compound

HRID 2224087Notes

Reaction equation

HRID 2224087 reaction equation
[I-].[C:2]1([S:8]([C:11]2[CH:29]=[CH:28][C:14]3[N:15]([C:21]4[CH:26]=[CH:25][N+:24]([CH3:27])=[CH:23][CH:22]=4)[CH2:16][C:17]([CH3:20])([CH3:19])[O:18][C:13]=3[CH:12]=2)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.C(O)C.[Pd]>[C:2]1([S:8]([C:11]2[CH:29]=[CH:28][C:14]3[N:15]([CH:21]4[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]4)[CH2:16][C:17]([CH3:19])([CH3:20])[O:18][C:13]=3[CH:12]=2)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 68432594HCID 68432594, compound

Product 1

HCID 58641516HCID 58641516, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 4-(7-benzenesulfonyl-2,2-dimethyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-1-methyl-pyridinium iodide (0.237 g., 0.452 mmol) in 10 mL methanol was added to a suspension of sodium borohydride (0.085 g., 2.260 mmol) in 10 mL methanol at 0C. The reaction was stirred at 0° C. for 3 hours, then stirred for 18 hours at room temperature. The reaction mixture was concentrated in vacuo and the resulting crude solid was dissolved in a mixture of 50 mL water and 50 mL ethyl acetate. The organic phase was washed twice with 50 mL ethyl acetate, and the combined organic phase was dried over sodium sulfate and concentrated in vacuo to give 187 mg. of a yellow foam. This foam was dissolved in 20 mL ethanol and added to 25 mg. of a 5% dispersion of palladium metal on charcoal suspended in 5 mL ethanol. The suspension was purged with hydrogen gas and maintained at a pressure of 55 psi for 48 hours. The reaction mixture was filtered through celite, concentrated in vacuo and purified by flash chromatography (12:1:0.1 CH2Cl2:MeOH:NH4OH) to give 114 mg (63%) of 7-benzenesulfonyl-2,2-dimethyl-4-(1-methyl-piperidin-4-yl)-3,4-dihydro-2H-benzo[1,4]oxazine as a clear oil. MS: 401 (M+H)+.

Workup

  1. stirringstirred for 18 hours at room temperature
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe resulting crude solid was dissolved in a mixture of 50 mL water and 50 mL ethyl acetate
  4. washThe organic phase was washed twice with 50 mL ethyl acetate
  5. dry with materialthe combined organic phase was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give 187 mg
  8. additionadded to 25 mg
  9. customThe suspension was purged with hydrogen gas
  10. temperaturemaintained at a pressure of 55 psi for 48 hours
  11. filtrationThe reaction mixture was filtered through celite
  12. concentrationconcentrated in vacuo
  13. custompurified by flash chromatography (12:1:0.1 CH2Cl2:MeOH:NH4OH)

Sources & evidence

ORD record
ord-101c225165c94d60b925b6b9e9d63c14
Source dataset
uspto-grants-2008_05
Patent number
US07378415B2

Reaction notes

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