Triphenylphosphine → 5-chloro-3-((1-t-butoxycarbonyl-2-(S)-pyrrolidinyl)methoxy)pyridine

HRID 1416594Notes

Reaction equation

HRID 1416594 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][OH:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:15][C:16]1[CH:17]=[C:18](O)[CH:19]=[N:20][CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>>[Cl:15][C:16]1[CH:17]=[C:18]([O:14][CH2:13][C@@H:9]2[CH2:10][CH2:11][CH2:12][N:8]2[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:19]=[N:20][CH:21]=1

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 5823053-Hydroxy-5-chloropyridineHCID 643448(S)-(-)-N-Boc-prolinolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 542993835-chloro-3-((1-t-butoxycarbonyl-2-(S)-pyrrolidinyl)methoxy)pyridineYield 60%

Procedure

(S)-1-t-Butoxycarbonyl-2-pyrrolidinemethanol (1.75 g, 8.71 mmol, prepared as in Example 11a) and 5-chloro-3-pyridinol (1.69 g, 13.10 mmol, Aldrich Chemical Co.). were allowed to react in the presence of triphenylphosphine and DEAD as described in Example 2a. The crude product was purified by chromatography over silica gel eluted with hexane/EtOAc to provide 1.49 g (60%) of the title compound as a pale yellow oil. TLC Rf 0.75 (1:1 EtOAc/Hex). MS (DCI/NH3) m/e 313 (M+H)+ with 35CI and m/e 315 (M+H)+ with 37Cl.

Workup

  1. customThe crude product was purified by chromatography over silica gel
  2. washeluted with hexane/EtOAc

Sources & evidence

ORD record
ord-106c62ce93f742f9bc5d9d0362dff5fb
Source dataset
uspto-grants-1999_06
Patent number
US05914328

Reaction notes

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