Sodium borohydride → HCID 71258196, compound

HRID 1506221Notes

Reaction equation

HRID 1506221 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C@@H:11]([CH3:14])[C@@H:10]([NH:15][C:16]2[C:21]([CH:22]=[O:23])=[CH:20][N:19]=[C:18]3[N:24]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[CH:25]=[CH:26][C:17]=23)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].CCCCCC.C(OCC)(=O)C>CO>[CH2:1]([N:8]1[CH2:13][CH2:12][C@@H:11]([CH3:14])[C@@H:10]([NH:15][C:16]2[C:21]([CH2:22][OH:23])=[CH:20][N:19]=[C:18]3[N:24]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:32])([CH3:34])[CH3:33])[CH:25]=[CH:26][C:17]=23)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21226206Ethyl acetate hexaneHCID 58078662HCID 58078662, compound

Product 1

HCID 71258196HCID 71258196, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

rac-4-{[(3R,4R)-1-Benzyl-4-methylpiperidin-3-yl]amino}-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (112 mg, 0.234 mmol) in methanol was stirred with sodium borohydride (13.3 mg, 0.351 mmol) at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure and, after addition of water, extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hi Flash column amino type manufactured by Yamazen Corporation: hexane/ethyl acetate=1/1 (v/v)) to give the title compound as a colorless oil (55 mg, yield 49%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionafter addition of water
  3. extractionextracted with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (Hi Flash column amino type

Sources & evidence

ORD record
ord-13da73e1f0f54d2e85fe215c5247de67
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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