Acetonitrile → HCID 67127711, compound

HRID 2167754Notes

Reaction equation

[CH2:1]([O:3][N:4]1[C:9]([CH3:11])([CH3:10])[CH2:8][C:7](=[O:12])[CH2:6][C:5]1([CH3:14])[CH3:13])[CH3:2].[C:15](#[N:17])[CH3:16].C([Li])CCC>C1COCC1>[CH2:1]([O:3][N:4]1[C:5]([CH3:13])([CH3:14])[CH2:6][C:7]([CH2:16][C:15]#[N:17])([OH:12])[CH2:8][C:9]1([CH3:11])[CH3:10])[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

3 g 1-Ethoxy-2,2,6,6-tetramethyl-piperidin-4-one is dissolved in 20 ml dry THF and 0.93 g acetonitrile are added. The mixture is cooled to −78° C. and 9.4 ml n-butyllithium (1.6 M solution in hexane) are added over a period of 30 min. Stirring is continued at −78° C. for 1 h, then the cooling bath is removed. After 2 h stirring at room temperature, the reaction mixture is diluted with MTBE and quenched with ammonium chloride solution. The organic phase is washed with water and brine, dried over sodium sulfate, and the solvent is removed in vacuo. The residue obtained is recrystallized from toluene to obtain the product as colorless crystals. 1H-NMR (CDCl3, 300 MHz): δ 3.78 (q, 2H), 2.43 (s, 2H), 1.93 (s, OH), 1.81 (2 d, 4H), 1.68 (d, 2H), 1.37 (s, 6H), 1.16 (s, 6H), 1.13 (t, 3H). C13-NMR (CDCl3, 75 MHz): δ 117.3, 72.5, 70.0, 58.8, 48.3, 34.8, 33.9, 21.1, 13.2. MS: m/z=241.0 [M+H]+.

Workup

customthe cooling bath is removed
stirringAfter 2 h stirring at room temperature
additionthe reaction mixture is diluted with MTBE
customquenched with ammonium chloride solution
washThe organic phase is washed with water and brine
dry with materialdried over sodium sulfate
customthe solvent is removed in vacuo
customThe residue obtained
customis recrystallized from toluene

Sources & evidence

ORD record: ord-7ed899d59da94828862cf4030a172eeb
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045480B2

Reaction notes

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