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

HRID 559345Notes

Reaction equation

HRID 559345 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)-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 saturated 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 saturated 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-a45b13cc20c64f359b82805ac1b974ec
Source dataset
uspto-grants-2011_11
Patent number
US08063042B2

Reaction notes

Loading…