Sodium borohydride → HCID 25228246, compound

HRID 1920678Notes

Reaction equation

HRID 1920678 reaction equation
[BH4-].[Na+].[CH:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[C:8]([C:19]#[N:20])[C:9]([O:15][CH2:16][O:17][CH3:18])=[CH:10][CH:11]=2)[N:6]=1)=[O:4]>C(O)C>[OH:4][CH2:3][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[C:8]([C:19]#[N:20])[C:9]([O:15][CH2:16][O:17][CH3:18])=[CH:10][CH:11]=2)[N:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 25228377HCID 25228377, compound

Product 1

HCID 25228246HCID 25228246, compoundYield 989.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Referring to FIG. 20, NaBH4 (0.0151 g, 0.400 mmol) was added to a solution of 9b (0.0240 g, 0.099 mmol) in ethanol (5 mL). The mixture was stirred for 20 min. The solvent was evaporated and the resulting residue was dissolved in chloroform, then washed with water followed by brine, dried over Na2SO4, concentrated, and purified by column chromatography (45:55 EtOAc/hexane) to yield 10b (0.0240 g, 0.98 mmol, 99%) as a white solid: 1H NMR (CDCl3) δ 8.14 (1H, d, J=8.0 Hz), 8.00 (1H, d, J=8.8 Hz), 7.56 (1H, d, J=9.6 Hz), 7.31 (1H, d, J=8.4 Hz), 5.46 (2H, s), 4.96 (2H, s), 3.59 (3H, s); 13C NMR (CDCl3) δ 202.5, 162.4, 147.6, 137.1, 133.9, 122.9, 118.3, 115.6, 114.6, 95.3, 64.4, 57.2; FTIR (neat) 2926, 1738, 1258, 1078, 795 cm−1; MS (ESI) m/z calculated for (C13H10N2O3+H)+ 245, found 245; HRMS (ESI) m/z calculated for (C13H10N2O3+H)+ 245.0922, found 245.0914.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe resulting residue was dissolved in chloroform
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by column chromatography (45:55 EtOAc/hexane)

Sources & evidence

ORD record
ord-4daf1ec3910a40878d3716c51c028402
Source dataset
uspto-grants-2012_05
Patent number
US08173620B2

Reaction notes

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