Water → 2-[(1-tert-butoxycarbonylpiperidin-4-ylcarbonyl)amino]-N-(5-chloropyridin-2-yl)-5-(1-hydroxyethyl)benzamide

HRID 1883050Notes

Reaction equation

HRID 1883050 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:20][C:21]([CH:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]2)=[O:22])=[C:8]([CH:19]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][N:13]=1)=[O:10])(=[O:3])[CH3:2].[BH4-].[Na+].O>CO>[C:32]([O:31][C:29]([N:26]1[CH2:27][CH2:28][CH:23]([C:21]([NH:20][C:7]2[CH:6]=[CH:5][C:4]([CH:1]([OH:3])[CH3:2])=[CH:19][C:8]=2[C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][N:13]=2)=[O:10])=[O:22])[CH2:24][CH2:25]1)=[O:30])([CH3:35])([CH3:33])[CH3:34]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 219061965-acetyl-2-[(1-tert-butoxycarbonylpiperidin-4-ylcarbonyl)amino]-N-(5-chloropyridin-2-yl)benzamide

Product 1

HCID 219062392-[(1-tert-butoxycarbonylpiperidin-4-ylcarbonyl)amino]-N-(5-chloropyridin-2-yl)-5-(1-hydroxyethyl)benzamideYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring solution of 5-acetyl-2-[(1-tert-butoxycarbonylpiperidin-4-ylcarbonyl)amino]-N-(5-chloropyridin-2-yl)benzamide (0.48 g, 0.96 mmol) in methanol (20 mL) was added sodium borohydride (36 mg, 0.96 mmol). The reaction was stirred at room temperature for 5 min, treated with water, and concentrated in vacuo. The residual mixture was partitioned between ethyl acetate and water and the layers separated. The organic phase was washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to give 0.47 g (98%) of a white foam.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residual mixture was partitioned between ethyl acetate and water
  3. customthe layers separated
  4. washThe organic phase was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3d48215aaabd407d88816609d7ea739c
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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