Sodium borohydride → HCID 59382996, compound

HRID 1254192Notes

Reaction equation

HRID 1254192 reaction equation
[C:1]([C:9]1([CH3:22])[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C1COCC1.CO>[OH:8][CH:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1([CH3:22])[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:10]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59382824Tert-butyl 3-benzoyl-3-methylpiperidine-1-carboxylate

Product 1

HCID 59382996HCID 59382996, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

tert-Butyl 3-benzoyl-3-methylpiperidine-1-carboxylate (278 mg, 0.92 mmol) was dissolved in 1:1 THF/MeOH (8 mL) and NaBH4 (70 mg, 1.84 mmol, 2 equiv) was added. After stirring 30 min at rt, LC-MS showed the reaction was complete. After concentration, the residue was partitioned between ether and diluted (˜1%) aq HCl. The aqueous layer was separated and extracted twice with ether. The combined organic layers were washed with satd aq NaHCO3, brine, dried over Na2SO4 and evaporated to afford crude product which was purified by chromatography on a 12-g prepacked silica gel cartridge eluted with a 0-35% EtOAc in hexanes gradient to afford tert-butyl 3-(hydroxy(phenyl)methyl)-3-methylpiperidine-1-carboxylate (198 mg, 71%). LC-MS (3 min) tR=1.83 min, m/z 328 (M+Na).

Workup

  1. additionwas added
  2. concentrationAfter concentration
  3. customthe residue was partitioned between ether
  4. additiondiluted (˜1%) aq HCl
  5. customThe aqueous layer was separated
  6. extractionextracted twice with ether
  7. washThe combined organic layers were washed with satd aq NaHCO3, brine
  8. dry with materialdried over Na2SO4
  9. customevaporated
  10. customto afford crude product which
  11. customwas purified by chromatography on a 12-g prepacked silica gel cartridge
  12. washeluted with a 0-35% EtOAc in hexanes gradient

Sources & evidence

ORD record
ord-1dbcc209315142a496249478be9ebd08
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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