5-Hydroxypipecolic acid → Methyl L-prolinate

Reaction equation

[CH3:1][O:2][C:3](=[O:12])[CH:4]1[CH2:9][CH2:8][CH:7]([O:10][CH3:11])C[NH:5]1.OC1CNC(C(O)=O)CC1>>[CH3:11][O:10][CH:7]1[NH:5][C@H:4]([C:3]([OH:2])=[O:12])[CH2:9][CH2:8]1.[CH3:1][O:2][C:3](=[O:12])[C@@H:4]1[CH2:9][CH2:8][CH2:7][NH:5]1

Participants

Reactant 2

HCID 1517305-Hydroxypipecolic acid

HCID 570630145-Methoxypipecolic acid methyl ester

Product 2

HCID 853477Methyl L-prolinate

HCID 705881305-Methoxyproline

Procedure

By substituting 5-methoxypipecolic acid methyl ester [prepared from 5-hydroxypipecolic acid by the procedure described in J. Chem. Soc. 429 (1945) for 5-methoxyproline] for the L-proline methyl ester in the procedure of Example 18, 2,3-dehydro-1-(3-acetylthio-1-oxopropyl)-5-methoxypipecolic acid is obtained.

Sources & evidence

ORD record: ord-287b883a75be461c8d84b27216c1c6b0
Source dataset: uspto-grants-1980_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04221912

Reaction notes

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