2,2,6-Trimethyl-4H-1,3-dioxin-4-one → 1-Acetoacetamido-2-acetoacetamidomethyl-3,3,5-trimethylcyclopentane

HRID 1060202Notes

Reaction equation

[NH2:1][CH:2]1[CH:6]([CH2:7][NH2:8])[C:5]([CH3:10])([CH3:9])[CH2:4][CH:3]1[CH3:11].[CH3:12][C:13]1[O:19]C(C)(C)[O:17][C:15](=O)[CH:14]=1>C1(C)C(C)=CC=CC=1>[C:15]([NH:1][CH:2]1[CH:3]([CH3:11])[CH2:4][C:5]([CH3:10])([CH3:9])[CH:6]1[CH2:7][NH:8][C:15](=[O:17])[CH2:14][C:13]([CH3:12])=[O:19])(=[O:17])[CH2:14][C:13]([CH3:12])=[O:19]

Participants

Conditions

Temperature: 113 °C

Procedure

To 5-amino-2,2,4-trimethylcyclopentylmethylamine (127.72 g, 0.819 mol) in xylene (525 ml) at 122° C. was added with stirring 2,2,6-trimethyl-1,3-dioxen-4-one (232.51 g, 1.637 mol) in xylene (525 mol) over 10 minutes, during which the temperature decreased to 104° C. After heating to 113° C. over 5 minutes, vigorous effervescence and distillation of acetone (through a Vigreux column) commenced. Pot temperature was increased to 127° C. over 5 minutes and to 140° C. over a further 30 minutes, with collection of acetone distillate. After cooling to 39° C., dichloromethane was added, and removal of solvent and drying (93° C./100 Pa) gave 1-acetoacetamido-2-acetoacetamidomethyl-3,3,5-trimethylcyclopentane (237.03 g, 89%), (AAMTCP), which was crushed to a light yellow powder, mp 94-114° C. (mixture of stereoisomers), and identified by 1H-NMR, 13C-NMR, FT-IR and Raman spectra.

Workup

customdecreased to 104° C
distillationvigorous effervescence and distillation of acetone (through a Vigreux column)
temperaturePot temperature was increased to 127° C. over 5 minutes and to 140° C. over a further 30 minutes, with collection of acetone distillate
temperatureAfter cooling to 39° C.
additiondichloromethane was added
customremoval of solvent
customdrying (93° C./100 Pa)

Sources & evidence

ORD record: ord-0c056279b81b4e8ebdc0090fc25f7189
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06521716B1

Reaction notes

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