(S)-(-)-N-Boc-prolinol → (R)-2-Methyl-3-(2-pyrrolidinylmethoxy)pyridine

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.ClC1C=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>>[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

Reactant 3

HCID 643448(S)-(-)-N-Boc-prolinol

HCID 688279N-(tert-Butoxycarbonyl)-D-prolinol

HCID 542993835-chloro-3-((1-t-butoxycarbonyl-2-(S)-pyrrolidinyl)methoxy)pyridine

Product 1

HCID 127922(R)-2-Methyl-3-(2-pyrrolidinylmethoxy)pyridine

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-80b6a394a4c94df6ab5e52b4ae96a0fd
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05948793

Reaction notes

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