1-Iodopropane → 2-Cyano-pentanoic acid tert-butyl ester

HRID 1480950Notes

Reaction equation

[CH2:1]1[CH2:11][CH2:10][N:9]2C(=NCCC2)[CH2:3][CH2:2]1.[C:12]([O:16][C:17](=[O:21])[CH2:18][C:19]#[N:20])([CH3:15])([CH3:14])[CH3:13].I[CH2:23][CH2:24][CH3:25]>CN(C=O)C.CCOC(C)=O>[C:12]([O:16][C:17](=[O:21])[C:11]([C:10]#[N:9])([CH2:1][CH2:2][CH3:3])[CH2:23][CH2:24][CH3:25])([CH3:13])([CH3:14])[CH3:15].[C:12]([O:16][C:17](=[O:21])[CH:18]([C:19]#[N:20])[CH2:2][CH2:1][CH3:11])([CH3:15])([CH3:14])[CH3:13]

Participants

Conditions

Temperature: 80 °C

Procedure

DBU was added slowly to a solution of cyano-acetic acid tert-butyl ester (6.03 g) in DMF (100 mL) at rt, followed by addition of 1-iodopropane (9.58 mL); the reaction mixture was stirred in an oil bath (bath temperature=80° C.) overnight subsequently. The reaction was cooled, diluted with EtOAc, then washed with cold water, dil. NaCl solution; EtOAc phase was dried over anhydrous sodium sulfate, filtered, concentrated, the residue was column purified to give 2-cyano-2-propyl-pentanoic acid tert-butyl ester (6.87 g) and 2-cyano-pentanoic acid tert-butyl ester (420 mg). 2-Cyano-2-propyl-pentanoic acid tert-butyl ester (1H NMR in CDCl3, δ in ppm) 1.502 (s, 9H), 1.9-1.2 (m, 8H), 0.96 (t, 6H, J=7.0 Hz). 2-Cyano-pentanoic acid tert-butyl ester (1H NMR in CDCl3, δ in ppm) 3.39 (t, 1H, J=7.0 Hz), 1.95-1.83 (m, 2H), 1.6-1.55 (m, 2H), 1.51 (s, 9H), 0.98 (t, 3H, J=7.2 Hz).

Workup

temperatureThe reaction was cooled
washwashed with cold water, dil. NaCl solution
dry with materialEtOAc phase was dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated
custompurified

Sources & evidence

ORD record: ord-cafe285eceea40f89d8b917093f5085f
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409892B2

Reaction notes

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