2-Propanaminium, N,N,N-tris(1,1-dimethylethyl)-2-methyl-, fluoride → 3-((trans-4-hydroxy-2-(S)-pyrrolidinyl)methoxy)pyridine

HRID 1416635Notes

Reaction equation

HRID 1416635 reaction equation
Cl.Cl.[OH:3][C@H:4]1[CH2:8][NH:7][C@H:6]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=CN=2)[CH2:5]1.[F-].[C:18]([N+:22](C(C)(C)C)(C(C)(C)C)C(C)(C)C)(C)(C)C>C1COCC1>[OH:3][C@H:4]1[CH2:8][NH:7][C@H:6]([CH2:9][O:10][C:11]2[CH:18]=[N:22][CH:14]=[CH:15][CH:16]=2)[CH2:5]1

Participants

4

Reactant 2

HCID 108690552-Propanaminium, N,N,N-tris(1,1-dimethylethyl)-2-methyl-, fluorideHCID 86754121(trans-4hydroxy-2-(S)-pyrrolidinyl)methoxypyridine dihydrochloride

Product 1

HCID 542026473-((trans-4-hydroxy-2-(S)-pyrrolidinyl)methoxy)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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.

Workup

  1. customthe volatiles were removed under vacuum
  2. customThe residue was purified on silica gel
  3. washeluting with 3:1 ethyl acetate

Sources & evidence

ORD record
ord-78fc82dea4fe4ac29c88121716436574
Source dataset
uspto-grants-1999_06
Patent number
US05914328

Reaction notes

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