Sodium borohydride → HCID 25228249, compound

HRID 1920687Notes

Reaction equation

HRID 1920687 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([N:12]([CH3:14])[CH3:13])=[CH:9][CH:10]=2)[N:5]=[C:4]([CH:15]=[O:16])[CH:3]=1.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([N:12]([CH3:13])[CH3:14])=[CH:9][CH:10]=2)[N:5]=[C:4]([CH2:15][OH:16])[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 25228248HCID 25228248, compound

Product 1

HCID 25228249HCID 25228249, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Referring to FIG. 21, compound 14b (50 mg, 0.213 mmol) was dissolved in absolute ethanol (2 mL). NaBH4 (8 mg, 0.213 mmol) was added to the solution and the mixture was stirred for 30 min. The solvent was evaporated and the residue dissolved in methanol and filtered. The filtrate was adsorbed onto silica gel and purified by column chromatography (7:3 EtOAc/hexane) to obtain 15b (30 mg, 0.126 mmol, 60%). 1H NMR (CDCl3) δ 8.02 (1H, d, J=8.8 Hz), 7.21 (1H, dd, J=9.2, 2.8 Hz), 7.11 (1H, d, J=2.8 Hz), 7.07 (1H, s), 4.81 (2H, s), 3.14, (6H, s); 13C NMR (CDCl3) δ 159.4, 152.1, 149.6, 143.1, 125.1, 117.9, 116.5, 114.3, 106.3, 64.2, 40.6; FTIR (neat) 2918, 1622, 1535, 1508, 1394, 1284, 1207, 1174, 1134; MS (ESI) m/z calculated for (C12H13ClN2O+H)+ 237, found 237; HRMS (ESI) m/z calculated for (C12H13ClN2O+H)+ 237.0838, found 237.0832.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in methanol
  3. filtrationfiltered
  4. custompurified by column chromatography (7:3 EtOAc/hexane)

Sources & evidence

ORD record
ord-c08bd77e337a42f48bd395e609ea410d
Source dataset
uspto-grants-2012_05
Patent number
US08173620B2

Reaction notes

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