Sodium borohydride → 1469777-40-9

HRID 2205637Notes

Reaction equation

HRID 2205637 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:29])[CH2:10][CH2:11][CH2:12][N:13]2[CH2:28][CH2:27][C@@H:16]3[N:17]4[C:26]5[C:25]([C@@H:15]3[CH2:14]2)=[CH:24][CH:23]=[CH:22][C:21]=5[NH:20][CH2:19][CH2:18]4)=[CH:5][CH:4]=1.[BH4-].[Na+]>CO>[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([OH:29])[CH2:10][CH2:11][CH2:12][N:13]2[CH2:28][CH2:27][C@@H:16]3[N:17]4[C:26]5[C:25]([C@@H:15]3[CH2:14]2)=[CH:24][CH:23]=[CH:22][C:21]=5[NH:20][CH2:19][CH2:18]4)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride3×HCID 86691453HCID 86691453, compound

Product 1

HCID 682319121469777-40-9Yield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(4-Fluoro-phenyl)-4-((6bR,10aS)-2,3,6b,9,10,10a-hexahydro-1H,7H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxalin-8-yl)-butan-1-one HCl salt (500 mg, 1.20 mmol) is suspended in 20 mL of methanol. NaBH4 (136 mg, 3.60 mmol) is added slowly into the suspension at room temperature. The suspension changed into a clear solution during the addition of NaBH4. After an hour, additional 90 mg of NaBH4 is added into the mixture to push the reaction to completion. The reaction mixture is quenched by adding 10 mL of water. After solvent is removed by rotary evaporation, the residue is treated with 10 mL of 1N NaOH aqueous solution, and then extracted with methylene chloride three times. The combined organic phase is washed with water, dried with anhydrous sodium sulfate, and then evaporated to dryness under vacuum to give 434 mg off-white foamy solids with 98% purity and 95% yield. MS (ESI) m/z 382.2 [M+H]+

Workup

  1. waitAfter an hour
  2. customthe reaction to completion
  3. customThe reaction mixture is quenched
  4. additionby adding 10 mL of water
  5. customAfter solvent is removed by rotary evaporation
  6. additionthe residue is treated with 10 mL of 1N NaOH aqueous solution
  7. extractionextracted with methylene chloride three times
  8. washThe combined organic phase is washed with water
  9. dry with materialdried with anhydrous sodium sulfate
  10. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-15608506ad334a398779e0c9b53c4b41
Source dataset
uspto-grants-2016_06
Patent number
US09371324B2

Reaction notes

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