(1-Methylcyclopropyl)methanol → HCID 118113349, compound

HRID 1485093Notes

Reaction equation

HRID 1485093 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8]1([CH2:11][OH:12])[CH2:10][CH2:9]1.Cl[C:14]1[N:19]=[CH:18][C:17]([C:20]([N:22]([O:24][CH3:25])[CH3:23])=[O:21])=[CH:16][CH:15]=1>O1CCCC1>[CH3:25][O:24][N:22]([CH3:23])[C:20]([C:17]1[CH:18]=[N:19][C:14]([O:12][CH2:11][C:8]2([CH3:7])[CH2:10][CH2:9]2)=[CH:15][CH:16]=1)=[O:21]

Participants

5

Reactant 3

HCID 137701(1-Methylcyclopropyl)methanolHCID 114355976-Chloro-N-methoxy-N-methylnicotinamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 118113349HCID 118113349, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of potassium tert-butoxide (1.68 g) in tetrahydrofuran (30 mL), a solution of 1-methylcyclopropanemethanol (1.29 g) in tetrahydrofuran (5 mL) was added and the mixture was stirred at room temperature for 10 minutes. After the reaction mixture was cooled to 0° C., a solution in tetrahydrofuran (5 mL) of the compound (3.00 g) obtained in step (1) above was added and after being brought to room temperature, the reaction mixture was stirred for an hour. The reaction mixture was then concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5-50:50) to give N-methoxy-N-methyl-6-[(1-methylcyclopropyl)methoxy]pyridine-3-carboxamide as a colorless oil (2.02 g).

Workup

  1. temperatureAfter the reaction mixture was cooled to 0° C.
  2. customafter being brought to room temperature
  3. stirringthe reaction mixture was stirred for an hour
  4. concentrationThe reaction mixture was then concentrated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5-50:50)

Sources & evidence

ORD record
ord-f8eaa44371694385ae506730233af711
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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