Dimethylformamide → HCID 87367896, compound

HRID 1673153Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)([CH3:10])[CH3:9])=[CH:4][CH:3]=1.C([Li])(CC)C.C1CCCCC1.CN([CH:30]=[O:31])C>O1CCCC1.C(OCC)(=O)C.O.C(O)(=O)C>[CH3:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([CH:30]=[O:31])=[CH:3][CH:4]=1)([N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[CH3:10]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of EXAMPLE 40B (0.4 g, 1.5 mmol)) in tetrahydrofuran (5 mL) was cooled to −78° C. and treated with a 1.3 M solution of sec-butyl lithium in cyclohexane (1.8 mL, 2.3 mmol). The mixture was stirred for 30 minutes at −78° C. and treated with N,N′-dimethylformamide (0.4 mL, 5.2 mmol). The mixture was warmed to ambient temperature over 1.5 hours, acetic acid (1 mL) added and the mixture stirred at ambient temperature for 10 minutes. Water (2 mL) was added and the mixture diluted with ethyl acetate. The organic layer was separated, washed with saturated sodium bicarbonate, water and brine, and concentrated. The residue was purified by flash chromatography on silica gel using 10-60% hexane/ethyl acetate to give the title compound (0.135 g, 42%). MS (ESI) m/e 218 (M+H)+.

Workup

temperatureThe mixture was warmed to ambient temperature over 1.5 hours
stirringthe mixture stirred at ambient temperature for 10 minutes
customThe organic layer was separated
washwashed with saturated sodium bicarbonate, water and brine
concentrationconcentrated
customThe residue was purified by flash chromatography on silica gel using 10-60% hexane/ethyl acetate

Sources & evidence

ORD record: ord-b91f25d757cc41f8be28b33baa2cfb72
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07999117B2

Reaction notes

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