Sodium borohydride → HCID 69435316, compound

HRID 404930Notes

Reaction equation

HRID 404930 reaction equation
[CH:1]([O:4][C:5]1[CH:24]=[CH:23][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[N:19]=[C:18]([C:20](=[O:22])[CH3:21])[S:17][N:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[BH4-].[Na+]>CO.O1CCCC1>[CH:1]([O:4][C:5]1[CH:24]=[CH:23][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[N:19]=[C:18]([CH:20]([OH:22])[CH3:21])[S:17][N:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 90195654HCID 90195654, compound

Product 1

HCID 69435316HCID 69435316, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 100C (1.7 g, 0.0047 mol) in a mixture of methanol and tetrahydrofuran (1:1) was added sodium borohydride (0.36 g, 0.0094 mol) and the reaction mixture was stirred at room temperature overnight. The solvent was removed and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated and purified on silica gel (ethyl acetate/hexane, 10˜50%) to give 1.43 g of product as a white solid (84% yield). 1H NMR (300 MHz, CDCl3) δ ppm 1.35 (d, J=5.88 Hz, 6H) 1.70 (d, J=6.62 Hz, 3H) 2.87 (s, 1H) 4.45-4.61 (m, 1H) 5.27 (q, J=6.62 Hz, 1H) 6.87-6.98 (m, 2 H) 7.16-7.25 (m, 2H) 7.94 (s, 1H). MS (ESI), M/Z: 364.0 (M+H)+.

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. custompurified on silica gel (ethyl acetate/hexane, 10˜50%)

Sources & evidence

ORD record
ord-2b44033309bd452e88bd4fdb8bcf6ed7
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

Loading…