(S)-(-)-N-Boc-prolinol → 2-methyl-3-(2-pyrrolidinylmethoxy)pyridine dihydrochloride, (R)-

HRID 1416603Notes

Reaction equation

HRID 1416603 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][OH:14])=O)(C)(C)C.[Cl:15]C1C=C(OC[C@@H]2CCCN2C(OC(C)(C)C)=O)C=NC=1.C(O[C:41]([N:43]1[CH2:47][CH2:46][CH2:45][C@H:44]1[CH2:48]O)=O)(C)(C)C>>[ClH:15].[ClH:15].[CH3:48][C:44]1[C:45]([O:14][CH2:13][C@H:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)=[CH:46][CH:47]=[CH:41][N:43]=1

Participants

4

Reactant 3

HCID 643448(S)-(-)-N-Boc-prolinolHCID 688279N-(tert-Butoxycarbonyl)-D-prolinolHCID 542993835-chloro-3-((1-t-butoxycarbonyl-2-(S)-pyrrolidinyl)methoxy)pyridine

Product 1

HCID 702036652-methyl-3-(2-pyrrolidinylmethoxy)pyridine dihydrochloride, (R)-

Procedure

Replacing (S)-1-t-butoxycarbonyl-2-pyrrolidinemethanol of Example 15 with (R)-1-t-butoxycarbonyl-2-pyrrolidinemethanol (Aldrich Chemical Co.), and following the procedure of steps 15a and 15b, the title compound was prepared. The MS and 1H NMR spectra were similar to compound 15a.

Sources & evidence

ORD record
ord-d56679b16d064fd0bbf48c82654bc6b0
Source dataset
uspto-grants-1999_06
Patent number
US05914328

Reaction notes

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