2-Propanaminium, N,N,N-tris(1,1-dimethylethyl)-2-methyl-, fluoride → 3-((trans-4-hydroxy-2-(S)-pyrrolidinyl)methoxy)pyridine
Reaction equation
C([N:11]1[CH2:15][C@H:14]([O:16][Si](C(C)(C)C)(C)C)[CH2:13][C@H:12]1[CH2:24][O:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)(OCC1C=CC=CC=1)=O.[F-].C([N+](C(C)(C)C)(C(C)(C)C)C(C)(C)C)(C)(C)C>C1COCC1>[OH:16][C@H:14]1[CH2:15][NH:11][C@H:12]([CH2:24][O:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH2:13]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A 1.35 g sample of the compound from step 72d above was dissolved in 9 mL of THF and 9.3 mL of tetra-(t-butyl)ammonium fluoride was added. The reaction mixture was stirred at room temperature for 16 hours, and the volatiles were removed under vacuum. The residue was purified on silica gel, eluting with 3:1 ethyl acetate:hexane, to give the title compound.