Tert-butyl[3-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-2-methyl-3-oxopropyl]carbamate → Tert-butyl 5-methyl-2,4-dioxopiperidine-1-carboxylate

HRID 589996Notes

Reaction equation

[C:1]([O:5][C:6](=[O:23])[NH:7][CH2:8][CH:9]([CH3:22])[C:10]([CH:12]1C(=O)OC(C)(C)[O:14][C:13]1=O)=[O:11])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C>[CH3:22][CH:9]1[CH2:8][N:7]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:23])[C:13](=[O:14])[CH2:12][C:10]1=[O:11]

Participants

Conditions

Temperature: 77 °C

Procedure

The tert-butyl[3-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-2-methyl-3-oxopropyl]carbamate from Step 1 (5.19 g, 15.76 mmol) was dissolved in ethyl acetate (60.6 ml), heated to reflux (77° C.) and stirred for 3 hrs, then cooled to room temperature. The solvent was evaporated under vacuum to afford the title compound as a yellow solid: 1H NMR (400 MHz, CDCl3) 4.29 (dd, J=14.0, 5.0 Hz, 1H), 3.53 (m, 3H), 2.59 (m, 114), 1.56 (s, 9H), 1.20 (d, J=7.1 Hz, 3H).

Workup

temperatureheated
temperaturecooled to room temperature
customThe solvent was evaporated under vacuum

Sources & evidence

ORD record: ord-d6e6e0f2bf224fd68b9c9c4a00dd0008
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233977B2

Reaction notes

Loading…