Boric Acid → 5-(1-Hydroxyethyl)-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

HRID 1623815Notes

Reaction equation

HRID 1623815 reaction equation
[BH4-].[Na+].B(O)(O)O.[C:7]([C:10]1[CH:11]=[CH:12][C:13]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:14]([CH:24]=1)[C:15]([NH:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)=[O:16])(=[O:9])[CH3:8]>C(O)C>[OH:9][CH:7]([C:10]1[CH:11]=[CH:12][C:13]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[C:14]([CH:24]=1)[C:15]([NH:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)=[O:16])[CH3:8]

Participants

5

Reactant 3

HCID 7628Boric AcidHCID 4311764Sodium borohydrideHCID 671072525-Acetyl-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

Product 1

HCID 671074715-(1-Hydroxyethyl)-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (32.8 mg, 0.87 mmol) and boric acid (53.6 mg, 0.87 mmol) were added to a suspension of 5-acetyl-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide (may be prepared as described in Example 72; 100 mg, 0.29 mmol) in ethanol (5 ml). The mixture was stirred for one hour and then it was quenched using saturated NaHCO3 solution (5 ml). The mixture was extracted with dichloromethane (3×5 ml). The organic layers were dried (MgSO4) and the solvent removed in vacuo. The residue was purified by MDAP to yield the title compound as a golden solid. 62 mg.

Workup

  1. customit was quenched
  2. extractionThe mixture was extracted with dichloromethane (3×5 ml)
  3. dry with materialThe organic layers were dried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by MDAP

Sources & evidence

ORD record
ord-5aa16436693c4693b7d93e2f7a745aea
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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