Triethylamine → 1-[tert-Butyl(dimethyl)silyl]-3-methylpyrrolidin-2-one

HRID 1014150Notes

Reaction equation

[CH3:1][CH:2]1[CH2:6][CH2:5][NH:4][C:3]1=[O:7].C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[Si:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>C(Cl)Cl.O>[CH3:28][C:27]([Si:24]([CH3:26])([CH3:25])[N:4]1[CH2:5][CH2:6][CH:2]([CH3:1])[C:3]1=[O:7])([CH3:30])[CH3:29]

Participants

Conditions

Temperature: 20 °C

Procedure

In an oven-dried 500 ml flask under argon was dissolved 3-methyl-2-pyrrolidinone (0.186 mol, 18.4 g) in 200 ml methylene chloride. To this solution was added Triethylamine (0.223 mol, 22.6 g), Dimethylaminopyridine (0.019 mol, 2.27 g), and t-Butyldimethylsilyl chloride (0.204 mol, 30.8 g). This mixture was stirred for 18 hrs at 20° C. after which time it was poured into 500 ml water, the organic layer separated, washed with water (2×100 ml), brine (100 ml), dried with MgSO4 and concentrated. Resulting crude oil was purified on 400 g silica (EtOAc/Hexanes) yielding 35.0 g (88%) of 1-[(1,1-dimethylethyl)(dimethyl)silyl]-3-methyl-2-pyrrolidinone a clear oil. LCMS (ESI+)=214 m/z (MH+). 1H NMR (400 MHz, CDCl3) δ 3.40-3.25 (m, 2H), 2.50-2.40 (m, 1H), 2.30-2.20 (m, 1H), 1.70-1.60 (m, 1H), 1.20-1.18 (d, 3H, J=7.06 Hz), 0.95 (s, 9H), 0.29-0.27 (d, 6H, J=6.70 Hz).

Workup

customthe organic layer separated
washwashed with water (2×100 ml), brine (100 ml)
dry with materialdried with MgSO4
concentrationconcentrated
customResulting crude oil
customwas purified on 400 g silica (EtOAc/Hexanes)

Sources & evidence

ORD record: ord-47f7adb98446461db3c142920ea9f881
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07982053B2

Reaction notes

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