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

HRID 655502Notes

Reaction equation

HRID 655502 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+]>O1CCCC1.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 tetrahydrofuran (15 ml) at −78° C. was added K-selectride (10.8 ml, 11 mmol, 1 M solution in tetrahydrofuran). After 2 h at −78° C. a few drops of water were cautiously added, the reaction allowed to reach room temperature, the tetrahydrofuran removed by evaporation and the residue the residue redissolved in dichloromethane, washed with sat. aq. sodium hydrogencarbonate solution, dried (Na2SO4) and concentrated. Purification by flash column chromatography (ethyl acetate/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 room temperature
  2. customthe tetrahydrofuran removed by evaporation
  3. dissolutionthe residue the residue redissolved in dichloromethane
  4. washwashed with sat. aq. sodium hydrogencarbonate solution
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customPurification by flash column chromatography (ethyl acetate/heptane 1:4)

Sources & evidence

ORD record
ord-2b676636e6be43a58bc984fe3564f1d1
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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