Water → HCID 89662286, compound

HRID 2275992Notes

Reaction equation

[CH3:1][C:2]1([CH3:22])[C:21]2[CH:9]3[N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:11](=[O:13])[CH2:12][CH:8]3[CH2:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.CC(O[CH:28](N(C)C)[N:29]([CH3:31])[CH3:30])(C)C.O>C1(C)C=CC=CC=1>[CH3:28][N:29](/[CH:31]=[C:12]1\[CH:8]2[CH2:7][C:6]3[CH2:5][CH2:4][CH2:3][C:2]([CH3:22])([CH3:1])[C:21]=3[CH:9]2[N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:11]\1=[O:13])[CH3:30]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of tert-butyl 8,8-dimethyl-2-oxo-3a,4,5,6,7,8b-hexahydro-3H-indeno[1,2-b]pyrrole-1-carboxylate (110 mg, 0.36 mmol) in toluene (2 mL) was added Bredereck reagent ((t-butoxybis(dimethylamino)methane) (0.30 mL, 1.44 mmol). The solution was heated to 110° C. for 5 h. The solution was cooled down to room temperature, and water was added. The solution was extracted with ethyl acetate, washed with brine, dried and concentrated. The residue was purified by flash chromatography eluting with cyclohexane and ethyl acetate (7/3 to 1/1) to give a white solid (83 mg, 64%). Mp 170-172° C.; LCMS (Method B) RT=1.14 min, 361 (M+H+); 1H NMR (400 MHz, CDCl3) δ 7.10 (1H, d, J=1.8 Hz), 5.27 (1H, d, J=8.1 Hz), 3.65 (1H, tt, J=8.1, 1.8 Hz), 2.99 (6H, s), 2.24 (1H, d, J=15.4 Hz), 1.75-1.97 (2H, m), 1.49-1.60 (11H, m), 1.38-1.46 (1H, m), 1.32 (1H, m), 1.19 (3H, s), 0.97 (3H, s) ppm.

Workup

temperatureThe solution was cooled down to room temperature
extractionThe solution was extracted with ethyl acetate
washwashed with brine
customdried
concentrationconcentrated
customThe residue was purified by flash chromatography
washeluting with cyclohexane and ethyl acetate (7/3 to 1/1)

Sources & evidence

ORD record: ord-d69f31b2738143c78c87f5e76c1eeb74
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09131688B2

Reaction notes

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