Water → N-(cyclopentylmethyl)-N-ethyl-6-methoxy-2-[(methoxymethoxy)methyl]pyridin-3-amine

HRID 906321Notes

Reaction equation

HRID 906321 reaction equation
[CH2:1]([NH:3][C:4]1[C:5]([CH2:12][O:13][CH2:14][O:15][CH3:16])=[N:6][C:7]([O:10][CH3:11])=[CH:8][CH:9]=1)[CH3:2].[CH:17]1([CH:22]=O)[CH2:21][CH2:20][CH2:19][CH2:18]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCCl>[CH:17]1([CH2:22][N:3]([CH2:1][CH3:2])[C:4]2[C:5]([CH2:12][O:13][CH2:14][O:15][CH3:16])=[N:6][C:7]([O:10][CH3:11])=[CH:8][CH:9]=2)[CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

6

Reactant 4

HCID 962WaterHCID 70106CyclopentanecarbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 672423343-Ethylamino-6-methoxy-2-(methoxymethyloxy)methylpyridine

Product 1

HCID 67242952N-(cyclopentylmethyl)-N-ethyl-6-methoxy-2-[(methoxymethoxy)methyl]pyridin-3-amineYield 86%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of N-ethyl-6-methoxy-2-[(methoxymethoxy)methyl]pyridin-3-amine (7.20 g, 31.8 mmol) and cyclopentanecarbaldehyde (3.75 g, 38.2 mmol) in 1,2-dichloroethane (240 mL) was added with sodium triacetoxyborohydride (8.75 g, 41.3 mmol), and the mixture was stirred at room temperature for 12 hours. The reaction mixture was added with water, and extracted with chloroform. The organic layers were combined, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1) to obtain N-(cyclopentylmethyl)-N-ethyl-6-methoxy-2-[(methoxymethoxy)methyl]pyridin-3-amine (8.39 g, 86%) as pale yellow oil.

Workup

  1. extractionextracted with chloroform
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-371592c16f744f918e01053be8940f76
Source dataset
uspto-grants-2011_09
Patent number
US08012989B2

Reaction notes

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