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

HRID 617343Notes

Reaction equation

HRID 617343 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]1

Participants

4

Reactant 2

HCID 108690552-Propanaminium, N,N,N-tris(1,1-dimethylethyl)-2-methyl-, fluorideHCID 18391718trans-3-((1-CBZ4-(t-butyldimethylsilyloxy)-2-(S)-pyrrolidinyl)methoxy)pyridine

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-7712e5a6f0ea4df39c74ad34728a088d
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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