1,3-Propanediamine, N1,N1,N3-trimethyl- → HCID 59909772, compound

HRID 2183043Notes

Reaction equation

[C:1]([O:5][C:6](=[O:28])[CH2:7][C@H:8]([C:18]1[O:22][N:21]=[C:20]([C:23]([O:25]CC)=O)[N:19]=1)[CH2:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)([CH3:4])([CH3:3])[CH3:2].[CH3:29][N:30]([CH3:36])[CH2:31][CH2:32][CH2:33][NH:34][CH3:35]>C(O)C>[CH:12]1([CH2:11][CH2:10][CH2:9][C@@H:8]([C:18]2[O:22][N:21]=[C:20]([C:23]([N:34]([CH2:33][CH2:32][CH2:31][N:30]([CH3:36])[CH3:29])[CH3:35])=[O:25])[N:19]=2)[CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:28])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

Conditions

Temperature: 85 °C

Procedure

A solution of ethyl 5-{(1R)-1-[2-(tert-butoxy)-2-oxoethyl]-4-cyclohexylbutyl}-1,2,4-oxadiazole-3-carboxylate (Preparation 3) (550 mg, 1.40 mmol) in ethanol (2 ml) was treated with N,N,N′-trimethyl-1,3-propanediamine (1.02 ml, 7.00 mmol) and the resulting mixture was heated at 85° C. in a sealed tube for 3 hours. The solvent removed under reduced pressure. The residue was purified by column chromatography on silica eluting with a gradient system of 97:3:0.3 (dichloromethane:methanol:ammonia) gradually changing to 90:10:1 (dichloromethane:methanol:ammonia) to afford the title compound as a colourless oil (512 mg).

Workup

customThe solvent removed under reduced pressure
customThe residue was purified by column chromatography on silica eluting with a gradient system of 97:3:0.3 (dichloromethane:methanol:ammonia)

Sources & evidence

ORD record: ord-ec93a86167874cfe913205617747af35
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06897306B2

Reaction notes

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