Trifluoroacetic acid → (S)-1-(4-undecylbenzoyl)pyrrolidine-2-carbonitrile

HRID 1484082Notes

Reaction equation

HRID 1484082 reaction equation
[C:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10]C(C)(C)C)=O)#[N:2].C(O)(C(F)(F)F)=O.[CH2:22]([C:33]1[CH:41]=[CH:40][C:36](C(O)=O)=[CH:35][CH:34]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>CCOC(C)=O>[CH2:22]([C:33]1[CH:34]=[CH:35][C:36]([C:8]([N:4]2[CH2:5][CH2:6][CH2:7][C@H:3]2[C:1]#[N:2])=[O:10])=[CH:40][CH:41]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 6951263tert-butyl (2S)-2-cyanopyrrolidine-1-carboxylateHCID 199790874-Undecylbenzoic acid

Product 1

HCID 68182743(S)-1-(4-undecylbenzoyl)pyrrolidine-2-carbonitrileYield 41%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

General procedure D was used to deprotect 0.447 grams (2.3 mmols) of 28. After standard work-up procedures, general procedure E was used to couple 2.3 mmols of the TFA salt of 28 to 0.635 grams (2.3 mmols) of 4-undecylbenzoic acid at 50° C. After work-up, 0.334 grams (0.94 mmols, 41%) of the title product was isolated as a yellow solid by flash chromatography (25% EtOAc in hexanes). 1H NMR (300 MHz, CDCl3) δ 7.24 (dd, J=12.2, 4.4 Hz, 2H), 7.04 (t, J=7.7 Hz, 2H), 4.97 (s, 1H), 3.88 (s, 1H), 3.31 (dt, J=18.1, 9.0 Hz, 1H), 2.77-2.64 (m, 1H), 2.63-2.54 (m, 1H), 2.24-2.12 (m, 1H), 1.60 (dt, J=15.1, 7.3 Hz, 4H), 1.29 (d, J=10.9 Hz, 14H), 0.88 (t, J=6.7 Hz, 3H). 13C NMR (126 MHz, CDCl3) δ 169.97, 146.29, 128.42, 128.18, 127.63, 127.17, 118.73, 49.51, 46.85, 46.20, 35.84, 31.91, 31.20, 30.27, 29.64, 29.61, 29.56, 29.46, 29.33, 29.23, 25.57, 22.68, 14.12.

Sources & evidence

ORD record
ord-0fc53b84f1fc49da84be35d34bbb7bf0
Source dataset
uspto-grants-2016_08
Patent number
US09421177B2

Reaction notes

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