Potassium;tri(butan-2-yl)boranuide → HCID 66782970, compound

HRID 1096185Notes

Reaction equation

HRID 1096185 reaction equation
[CH2:1]([N:8]1[CH2:13][C@@H:12]([CH3:14])[CH2:11][C:10](=[O:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCC(C)[BH-](C(C)CC)C(C)CC.[K+]>C1COCC1.O>[CH2:1]([N:8]1[CH2:13][C@@H:12]([CH3:14])[CH2:11][C@H:10]([OH:15])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 4304157Potassium;tri(butan-2-yl)boranuideHCID 66782705HCID 66782705, compound

Product 1

HCID 66782970HCID 66782970, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-1-benzyl-5-methyl-piperidin-3-one (1.1 g, 5 mmol) in dry THF (15 ml) at −78° C. was added K-selectride (10.8 ml, 11 mmol, 1 M solution in THF). After 2 h at −78° C. a few drops of water were cautiously added, the reaction allowed to reach RT, the THF removed by evaporation and the residue the residue redissolved in CH2Cl2, washed with sat. aq. NaHCO3 solution, dried (Na2SO4) and concentrated. Purification by flash column chromatography (EtOAc/heptane 1:4) afforded the titled product as a crystalline solid (0.9 g, 43%). MS (ISP)=204.3 (M+H)+.

Workup

  1. customto reach RT
  2. customthe THF removed by evaporation
  3. dissolutionthe residue the residue redissolved in CH2Cl2
  4. washwashed with sat. aq. NaHCO3 solution
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customPurification by flash column chromatography (EtOAc/heptane 1:4)

Sources & evidence

ORD record
ord-e491eca7e7f342acb323ea3942daa9f8
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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