Dimethylformamide → HCID 59150482, compound

HRID 1668601Notes

Reaction equation

[CH3:1][CH:2]([NH:4][C:5]([C:7]1[CH:24]=[CH:23][C:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15][C:9]=2[CH:8]=1)=[O:6])[CH3:3].[Li]C(C)(C)C.CN([CH:33]=[O:34])C>C1COCC1>[OH:34][CH:33]1[C:24]2[CH:23]=[C:10]3[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15][C:9]3=[CH:8][C:7]=2[C:5](=[O:6])[N:4]1[CH:2]([CH3:1])[CH3:3]

Participants

Conditions

Temperature: -40 °C

Procedure

To a solution of 1,1-dimethylethyl 7-{[(1-methylethyl)amino]carbonyl}-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (0.95 g, 1 eq) in THF (50 ml), cooled to −78° C. under nitrogen atmosphere, t-BuLi (1.7 M pentane solution, 3.7 ml) was added over a 20 min period, then the mixture was allowed to warm to −40° C. and stirred for 1 h at that temperature. Anhydrous DMF (0.27 ml) was added dropwise, then the mixture was allowed to warm to room temperature and quenched with a saturated aqueous solution of NH4Cl (5 ml). After removal of THF, the residue was dissolved in ethyl acetate and the solution washed with 1 N HCl, 5% aqueous NaHCO3 and brine, then dried over Na2SO4 and concentrated to afford a white solid (1.0 g, 97% yield).

Workup

temperatureto warm to room temperature
customquenched with a saturated aqueous solution of NH4Cl (5 ml)
customAfter removal of THF
dissolutionthe residue was dissolved in ethyl acetate
washthe solution washed with 1 N HCl, 5% aqueous NaHCO3 and brine
dry with materialdried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-ac3f92cd8fa441e8b2e1b08373286ce1
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989444B2

Reaction notes

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