3-Hydroxypyridine → HCID 19874726, compound

HRID 465515Notes

Reaction equation

HRID 465515 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:27]([CH2:29][CH2:30][CH:31](O)[CH2:32][CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])#[N:28]>>[NH2:28][CH2:27][CH2:29][CH2:30][CH:31]([O:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)[CH2:32][CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36]

Participants

4

Reactant 3

HCID 79713-HydroxypyridineHCID 11776TriphenylphosphineHCID 19874697HCID 19874697, compound

Product 1

HCID 19874726HCID 19874726, compound

Procedure

Hex-5-enoic acid is first converted to the corresponding epoxide with e.g. m-chloroperbenzoic acid and esterified with diazomethane to the methyl ester which is then condensed with acetonitrile in the presence of lithium diisopropylamide (LDA) to yield methyl 7-cyano-5-hydroxy-heptanoate. Condensation with 3-hydroxypyridine in the presence of triphenylphosphine and reduction of the nitrile yields methyl 8-amino-5-(3-pyridyloxy)-octanoate.

Sources & evidence

ORD record
ord-9b6c7b13793848a0880219606dcc844f
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

Loading…