Chlorotrimethylsilane → tert-Butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 2406235Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[Si:16]([CH3:19])([CH3:18])[CH3:17].CCN(CC)CC>CN(C=O)C.CCOCC>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[C:11]([O:14][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

4-Oxo-piperidine-1-carboxylic acid tert-butyl ester (10.0 g, 501 mmol) was dissolved in DMF (20 mL). Chlorotrimethylsilane (6.6 g, 60.6 mmol) was added, followed by Et3N (12.3 g, 122 mmol). The mixture was stirred at 80° C. for 16 hours, cooled to ambient temperature, diluted with Et2O, and then washed with water, followed by brine. The organic layer was separated, dried over Na2SO4, filtered and concentrated. Purification by flash chromatography on silica gel (EtOAc/heptanes 0-50%) afforded 4-trimethylsilanyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (4.3 g, 32% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.80 (br. s., 1H), 3.88 (br. s., 2H), 3.53 (t, J=5.81 Hz, 2H), 2.11 (br. s., 2H), 1.49 (s, 9H), 0.20 (s, 9H).

Workup

temperaturecooled to ambient temperature
washwashed with water
customThe organic layer was separated
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customPurification by flash chromatography on silica gel (EtOAc/heptanes 0-50%)

Sources & evidence

ORD record: ord-193327e23ec842d59bf841f8285ab5ca
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809352B2

Reaction notes

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