6-Oxa-3-azabicyclo[3.1.1]heptane → HCID 68934760, compound

HRID 331835Notes

Reaction equation

HRID 331835 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][O:14][C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=3)=[C:11]([CH3:24])[O:10][N:9]=2)=[CH:4][CH:3]=1.[CH:25]12[CH2:31][CH:29]([O:30]1)[CH2:28][NH:27][CH2:26]2>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH2:13][O:14][C:15]3[N:16]=[CH:17][C:18]([C:19]([N:27]4[CH2:26][C@@H:25]5[CH2:31][C@@H:29]([O:30]5)[CH2:28]4)=[O:21])=[CH:22][CH:23]=3)=[C:11]([CH3:24])[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 179658576-Oxa-3-azabicyclo[3.1.1]heptaneHCID 684418986-[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-nicotinic acid

Product 1

HCID 68934760HCID 68934760, compoundYield 22%

Procedure

As described for example 105, 6-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-nicotinic acid (36 mg, 0.11 mmol) was converted, using rac-6-oxa-3-aza-bicyclo[3.1.1]heptane instead of 2,2,2-trifluoroethylamine, to the title compound (10 mg, 22%) which was obtained as a colourless gum. MS: m/e=410.4 [M+H]+.

Sources & evidence

ORD record
ord-4a0e04a285d9481aada23010f3a77093
Source dataset
uspto-grants-2014_11
Patent number
US08877782B2

Reaction notes

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