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

HRID 617295Notes

Reaction equation

HRID 617295 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 15a) 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 35Cl 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-d62a91b2cdd449f98c7d09e38c1cdaa7
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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