Cyclohexanecarboxaldehyde → HCID 11418778, compound

HRID 639550Notes

Reaction equation

HRID 639550 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([NH:15][CH2:16][CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[O:14])[C:5](=[O:12])[N:6]([CH:9]([CH3:11])[CH3:10])[C:7]=1[CH3:8].[CH:23]1([CH:29]=O)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([NH:15][CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([CH2:29][CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH2:19][CH2:18]2)=[O:14])[C:5](=[O:12])[N:6]([CH:9]([CH3:10])[CH3:11])[C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 16275CyclohexanecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 59255051HCID 59255051, compound

Product 1

HCID 11418778HCID 11418778, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-chloro-1-isopropyl-6-methyl-2-oxo-N-(piperidin-4-ylmethyl)-1,2-dihydropyridine-3-carboxamide as prepared in 6(2) (228 mg, 0.70 mmol), cyclohexanecarboxaldehyde (94 mg, 0.84 mmol) in dichloromethane (11 mL) was added sodium triacetoxyborohydride (312 mg, 1.40 mmol) at room temperature, and the mixture was stirred at room temperature for 4 h. The mixture was quenched with saturated sodium hydrogencarbonate aqueous solution (80 mL), extracted with dichloromethane (50 mL×4). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The residue was chromatographed on a column of silica gel eluting with dichloromethane/methanol (v/v=20/1) to give 213 mg (72%) of the title compound as a white solid.

Workup

  1. customThe mixture was quenched with saturated sodium hydrogencarbonate aqueous solution (80 mL)
  2. extractionextracted with dichloromethane (50 mL×4)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on a column of silica gel eluting with dichloromethane/methanol (v/v=20/1)

Sources & evidence

ORD record
ord-29a50eaf63a544cb82f44633bc0713f1
Source dataset
uspto-grants-2010_04
Patent number
US07691881B2

Reaction notes

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