Oxolan-3-amine → HCID 59448141, compound

HRID 1920928Notes

Reaction equation

HRID 1920928 reaction equation
CO[C:3]([C:5]1[O:9][N:8]=[C:7]([O:10][CH2:11][C:12]2[C:13]([CH2:18][CH2:19][CH2:20][CH3:21])=[N:14][O:15][C:16]=2[CH3:17])[CH:6]=1)=[O:4].[NH2:22][CH:23]1[CH2:27][CH2:26][O:25][CH2:24]1>>[CH:13]([NH2:14])([CH3:18])[CH3:12].[O:25]1[CH2:26][CH2:27][CH:23]([NH:22][C:3]([C:5]2[O:9][N:8]=[C:7]([O:10][CH2:11][C:12]3[C:13]([CH2:18][CH2:19][CH2:20][CH3:21])=[N:14][O:15][C:16]=3[CH3:17])[CH:6]=2)=[O:4])[CH2:24]1

Participants

4

Reactant 2

HCID 3365553Oxolan-3-amineHCID 67491973HCID 67491973, compound

Product 2

HCID 6363IsopropylamineHCID 59448141HCID 59448141, compoundYield 164.6%

Procedure

As described for example 28, 3-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl ester (377 mg, 1.28 mmol), was converted using 3-aminotetrahydrofuran (335 mg, 3.84 mmol), instead of isopropyl amine, to the title compound (368 mg, 82%) which was obtained as a colourless gum after purification by chromatography (silica, heptane:ethyl acetate=4:1 to 4:1). MS: m/e=350.4 [M+H]+.

Sources & evidence

ORD record
ord-f18036c861d84cf2a38dbe6e54d0f0bc
Source dataset
uspto-grants-2012_05
Patent number
US08173652B2

Reaction notes

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