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Pyridine → 5-chloro-3-((1-methyl-2-(R)-pyrrolidinyl)methoxy)pyridine

HRID 617308
Notes
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Reaction equation

HRID 617308 reaction equation
N1C=CC=CC=1.[Cl:7][C:8]1[CH:9]=[C:10]([O:14][CH2:15][C@H:16]2[CH2:20][CH2:19][CH2:18][N:17]2[C:21](OC(C)(C)C)=O)[CH:11]=[N:12][CH:13]=1.ClC1C=C(OC[C@@H]2CCCN2C)C=NC=1>CO.C(Cl)(Cl)Cl>[Cl:7][C:8]1[CH:9]=[C:10]([O:14][CH2:15][C@H:16]2[CH2:20][CH2:19][CH2:18][N:17]2[CH3:21])[CH:11]=[N:12][CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 21309710(R)-tert-butyl 2-((5-chloropyridin-3-yloxy)methyl)pyrrolidine-1-carboxylateHCID 443189813-Chloro-5-((S)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridine

Product 1

HCID 541499775-chloro-3-((1-methyl-2-(R)-pyrrolidinyl)methoxy)pyridine

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanol
Solvent

Procedure

Following the procedure of Example 16a, replacing the 5-chloro-3-(N-t-butoxycarbonyl-2-S)-pyrrolidinylmethoxy)pyridine thereof with 5-chloro-3-(N-t-butoxycarbonyl-2-(R)-pyrrolidinylmethoxy)pyridine (prepared from the (R)-isomer of the starting material following the procedure of Example 15a), the tide compound was prepared. TLC Rf =0.23 (10% MeOH/CHCl3). MS and 1H NMR (CDCl3, 300 MHz) are similar to 16a.

Workup

  1. customwas prepared

Sources & evidence

ORD record
ord-1af3f47d8cce4af389c7692eae79faaf
Source dataset
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05948793

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes