Pyridine → HCID 23582346, compound

HRID 1259031Notes

Reaction equation

HRID 1259031 reaction equation
[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH:5]3[NH:12][C:13]([N:15]3[CH2:20][CH2:19][CH2:18][C@H:17]([CH3:21])[CH2:16]3)=[O:14])[CH2:3]1)[CH2:9]2.[C:22](Cl)(=[O:24])[CH3:23].N1C=CC=CC=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:21][C@H:17]1[CH2:18][CH2:19][CH2:20][N:15]([C:13]([NH:12][CH:5]2[CH:4]3[CH2:3][C:2]4([O:1][C:22](=[O:24])[CH3:23])[CH2:9][CH:8]([CH2:7][CH:6]2[CH2:11]4)[CH2:10]3)=[O:14])[CH2:16]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 86634270HCID 86634270, compound

Product 1

HCID 23582346HCID 23582346, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (S)-3-Methyl-piperidine-1-carboxylic acid (5-hydroxy-adamantan-2-yl)-amide 0.15 g (0.51 mmol), 0.109 ml of acetyl chloride, 0.3 ml of pyridine in 1.5 ml of methylene chloride was stirred at room temperature overnight. A saturated NaHCO3 solution was added, the organic phase extracted with methylene chloride, washed with HCl 1 N solution and dried over sodium sulphate. Flash chromatography on silica gel (eluant CH2Cl2/MeOH: 95/05) yielded 75 mg of the title compound

Workup

  1. extractionthe organic phase extracted with methylene chloride
  2. washwashed with HCl 1 N solution
  3. dry with materialdried over sodium sulphate

Sources & evidence

ORD record
ord-495814e89c5e4978a795b2710750942b
Source dataset
uspto-grants-2013_06
Patent number
US08466200B2

Reaction notes

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