Methanol → 1-[5-(Tert-butyldimethylsilanyloxymethyl)pyridin-2-yl]cyclopropylacetamide

HRID 76356Notes

Reaction equation

HRID 76356 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2(N)[CH2:18][CH2:17]2)=[N:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:20]([O:23]C(=O)C)(=O)[CH3:21].CO.[N:29]1C=CC=CC=1>CN(C)C1C=CN=CC=1>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2([CH2:21][C:20]([NH2:29])=[O:23])[CH2:18][CH2:17]2)=[N:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 594069831-[5-(Tert-butyldimethylsilanyloxymethyl)pyridin-2-yl]cyclopropylamine

Product 1

HCID 684316481-[5-(Tert-butyldimethylsilanyloxymethyl)pyridin-2-yl]cyclopropylacetamide

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

1-[5-(tert-Butyldimethylsilanyloxymethyl)pyridin-2-yl]cyclopropylamine (190 mg) was dissolved in pyridine (2 ml), acetic anhydride (0.13 ml) and 4-dimethylaminopyridine (17 mg) were added, and the mixture was stirred at room temperature for 4 hr. Methanol (2 ml) was added and the mixture was stirred for about 10 min. The solvent was evaporated, and the residue was purified by column chromatography (Yamazen HI-FLASH™ COLUMN size L, elution solvent: hexane/ethyl acetate) to give the title compound (158 mg).

Workup

  1. stirringthe mixture was stirred for about 10 min
  2. customThe solvent was evaporated
  3. customthe residue was purified by column chromatography (Yamazen HI-FLASH™ COLUMN size L, elution solvent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-84ff4a2c61db41a8b010e17651ac0d68
Source dataset
uspto-grants-2014_09
Patent number
US08835631B2

Reaction notes

Loading…