1-[2-(Tert-butyldimethylsilyloxymethyl)pyridin-5-yl](1-methyl)ethylamine → (5-(2-Aminopropan-2-yl)pyridin-2-yl)methanol

HRID 2183498Notes

Reaction equation

HRID 2183498 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([NH2:19])([CH3:18])[CH3:17])=[CH:12][N:11]=1)(C(C)(C)C)(C)C>CC(O)=O.C1COCC1.O>[OH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([NH2:19])([CH3:17])[CH3:18])=[CH:12][N:11]=1

Participants

5

Reactant 1

HCID 697956161-[2-(Tert-butyldimethylsilyloxymethyl)pyridin-5-yl](1-methyl)ethylamine

Product 1

HCID 69793455(5-(2-Aminopropan-2-yl)pyridin-2-yl)methanolYield 37.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-[2-(tert-butyldimethylsilyloxymethyl)pyridin-5-yl](1-methyl)ethylamine (1.5 g, 5.35 mmol) in AcOH (15 ml), THF (5 ml) and H2O (5 ml) was heated at 50° C. for 2.5 h. The resultant mixture was concentrated under reduced pressue and then azeotroped with toluene (2×50 ml). The residue was dissolved in CH2Cl2 (15 ml) and MeOH (15 ml) and dry loaded onto silica. Purification by column chromatography on silica, using 10% MeOH/CH2Cl2 containing 1% NH3 solution as eluent, gave the desired alcohol (330 mg, 37%).

Workup

  1. concentrationThe resultant mixture was concentrated under reduced pressue
  2. customazeotroped with toluene (2×50 ml)
  3. dissolutionThe residue was dissolved in CH2Cl2 (15 ml)
  4. dry with materialMeOH (15 ml) and dry
  5. customPurification by column chromatography on silica

Sources & evidence

ORD record
ord-dbb84f2cf53c434e8b689a1cea340615
Source dataset
uspto-grants-2005_05
Patent number
US06900209B2

Reaction notes

Loading…