Potassium tert-butoxide → HCID 86680441, compound

HRID 1184579Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:23])[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH:7]1[C:19]([O:21]C)=O.CC(C)([O-])C.[K+]>O1CCCC1>[O:21]=[C:19]1[CH:7]2[CH2:8][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:10][CH2:11][N:6]2[CH2:5][CH:4]1[C:3]([O:2][CH3:1])=[O:23]

Participants

Conditions

Temperature: 2.5 °C

Procedure

To a solution of 1-tert-butyl 3-methyl 4-(3-methoxy-3-oxopropyl)piperazine-1,3-dicarboxylate (Example 100A, 180 g, 0.545 mol) in tetrahydrofuran (1.3 L) was added potassium t-butoxide (98 g, 0.872 mol) with stirring at 0-5° C. under N2 atmosphere portion-wise over a period of 30 minutes. The reaction mixture was stirred at ambient temperature for 2 hours. The reaction was then quenched with saturated aqueous ammonium chloride solution (500 mL) and extracted with ethyl acetate (1 L). The organic layer was separated, washed with brine (500 mL), dried over Na2SO4, filtered and concentrated to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.48 (s, 9H), 2.28-2.35 (m, 2H), 2.65-2.83 (m, 1H), 2.83-3.12 (m, 3H), 3.43 (t, 1H, J=8.4 Hz), 3.61 (t, 1H, J=8.4 Hz), 3.78 (s, 3H), 3.98-4.20 (bs, 1H), 4.20-4.45 (bs, 1H).

Workup

stirringThe reaction mixture was stirred at ambient temperature for 2 hours
customThe reaction was then quenched with saturated aqueous ammonium chloride solution (500 mL)
extractionextracted with ethyl acetate (1 L)
customThe organic layer was separated
washwashed with brine (500 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-89395c5df5804405981a87d994801d81
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669255B2

Reaction notes

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