HCID 15336555, compound → HCID 53714875, compound

HRID 1078261Notes

Reaction equation

[CH2:1](C1C2N=C(OC)C=CC=2CC2(OCCO2)C1)C.[CH3:19][O:20][C:21]([C:23]12[C:38](=[O:39])[CH:27]([CH:28]([CH3:37])[C:29]3[C:34]1=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[N:30]=3)[CH2:26][C:25](=[CH2:40])[CH2:24]2)=[O:22]>>[CH3:19][O:20][C:21]([C:23]12[C:38](=[O:39])[CH:27]([CH:28]([CH2:37][CH3:1])[C:29]3[C:34]1=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[N:30]=3)[CH2:26][C:25](=[CH2:40])[CH2:24]2)=[O:22]

Participants

Reactant 2

HCID 15336555HCID 15336555, compound

HCID 54167166HCID 54167166, compound

Product 1

HCID 53714875HCID 53714875, compound

Procedure

10-Ethyl-7,8,9,10-tetrahydro-2-methoxy-7-methylene-11-oxo-5,9-methanocycloocta[b]pyridine-5(6H)-carboxylic Acid Methyl Ester (6c) was prepared from 4c in the same manner as described for the preparation of compound 6b: IR (neat) 2953, 1743, 1724, 1601, 1577, 1479, 823 cm-1 ; 1H NMR (major isomer) δ6.94 (d, 1H, J=8.7 Hz), 6.56 (d, 1H, J=8.7 Hz), 4.73 (s, 1H), 4.41 (s, 1H), 3.87 (s, 3H), 3.77 (s, 3H), 3.01 (m, 1H), 2.90 (m, 2H), 2.75 (m, 1H), 2.55 (m, 2H), 1.85 (m, 1H), 1.60 (m, 1H), 1.22 (t, 3H, J=7.4 Hz); 13C NMR δ209.0, 208.6, 171.5, 171.4, 162.9, 162.4, 155.2, 154.2, 139.3, 139.1, 137.3, 124.6, 124.2, 115.9, 115.7, 109.7, 62.9, 62.3, 53.4, 53.3, 53.0, 52.6, 50.0, 48.1, 47.6, 47.3, 43.5, 36.0, 29.9, 21.6, 11.6, 11.4; MS m/z 315 (M+), 287, 256, 228.

Sources & evidence

ORD record: ord-4e7ef829500144098342af8a7787b6fd
Source dataset: uspto-grants-1996_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05547960

Reaction notes

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