Sodium borohydride → HCID 118441539, compound

HRID 629816Notes

Reaction equation

HRID 629816 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([C@:7]23[CH2:15][O:14][C@@H:13]([CH3:16])[CH2:12][C@H:11]2[CH2:10][O:9][NH:8]3)[S:5][CH:6]=1.[BH4-].[Na+]>C(#N)C.O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo]>[NH2:8][C@@:7]1([C:4]2[S:5][CH:6]=[C:2]([Br:1])[N:3]=2)[CH2:15][O:14][C@@H:13]([CH3:16])[CH2:12][C@H:11]1[CH2:10][OH:9]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 118435585HCID 118435585, compound

Product 1

HCID 118441539HCID 118441539, compound

Reagents, catalysts & solvents 3

HCID 98885Molybdenum carbonyl (Mo(CO)6)CatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Molybdenum hexacarbonyl (98%, 6.67 g, 24.8 mmol) was added to a solution of C3 (15.12 g, 49.54 mmol) in a mixture of acetonitrile (390 mL) and water (20 mL), and the reaction mixture was heated at reflux for 1 hour. After cooling to room temperature, the reaction mixture was chilled in an ice bath, treated portion-wise with sodium borohydride (7.50 g, 198 mmol), and allowed to stir at 0° C. for 1 hour. The mixture was then filtered through a pad of diatomaceous earth, and the pad was washed three times with dichloromethane; the organic portion of the combined filtrate and washes was washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated in vacuo. Methanol was added to the residue, then removed via concentration under reduced pressure. This methanol treatment was repeated, and the resulting residue was dissolved in dichloromethane, washed twice with 1 M aqueous sodium hydroxide solution, washed once with saturated aqueous sodium chloride solution and concentrated in vacuo, affording the product as a brown solid. Yield: 14.48 g, 47.13 mmol, 95%. LCMS m/z 307.0, 309.0 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 7.22 (s, 1H), 3.79 (d, half of AB quartet, J=11.5 Hz, 1H), 3.64-3.75 (m, 3H), 3.54 (dd, half of ABX pattern, J=11.5, 4.1 Hz, 1H), 2.46-2.54 (m, 1H), 1.82-1.94 (m, 1H), 1.67-1.74 (m, 1H), 1.32 (d, J=6.2 Hz, 3H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 1 hour
  3. temperaturethe reaction mixture was chilled in an ice bath
  4. filtrationThe mixture was then filtered through a pad of diatomaceous earth
  5. washthe pad was washed three times with dichloromethane
  6. washthe organic portion of the combined filtrate and washes was washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. additionMethanol was added to the residue
  11. customremoved via concentration under reduced pressure
  12. dissolutionthe resulting residue was dissolved in dichloromethane
  13. washwashed twice with 1 M aqueous sodium hydroxide solution
  14. washwashed once with saturated aqueous sodium chloride solution
  15. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-38bf906da63a4d0cab6e8f91b8a118dd
Source dataset
uspto-grants-2016_04
Patent number
US09315520B2

Reaction notes

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