Acetic Acid → HCID 69436029, compound

HRID 1890643Notes

Reaction equation

HRID 1890643 reaction equation
[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[CH:17][CH:16]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2].C(O)(=O)C.[CH3:32][N:33]1[CH2:38][CH2:37][C:36](=O)[CH2:35][CH2:34]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClC(Cl)C>[CH2:1]([C:3]1[N:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH:22]3[CH2:27][CH2:26][N:25]([CH:36]4[CH2:37][CH2:38][N:33]([CH3:32])[CH2:34][CH2:35]4)[CH2:24][CH2:23]3)=[CH:17][CH:16]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 740491-Methyl-4-piperidoneHCID 5049666Sodium triacetoxyborohydrideHCID 23156153HCID 23156153, compound

Product 1

HCID 69436029HCID 69436029, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of Compound 140 (0.100 g, 0.28 mmol) in dichloroethane was added with acetic acid (0.48 mL, 0.84 mmol) and 1-methyl-4-piperidone (0.84 mL, 0.68 mmol). After 20 minutes, the mixture was added with sodium triacetoxyborohydride (0.0827 g, 0.39 mmol) followed by stirring at room temperature overnight. The reaction mixture was added with a 2 mol/L aqueous sodium hydroxide solution, and extracted with chloroform three times. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from diisopropyl ether-ethanol to obtain Compound 141 (0.0767 g, 0.17 mmol, 59%).

Workup

  1. extractionextracted with chloroform three times
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was recrystallized from diisopropyl ether-ethanol

Sources & evidence

ORD record
ord-550b0225173c43c68a8060504d56b384
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

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