p-Octylbenzoic acid → (S)-1-(4-octylbenzoyl)pyrrolidine-2-carbonitrile

HRID 1484083Notes

Reaction equation

HRID 1484083 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].[CH2:15]([C:23]1[CH:31]=[CH:30][C:26](C(O)=O)=[CH:25][CH:24]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>ClCCl.FC(F)(F)C(O)=O.CCOC(C)=O>[CH2:15]([C:23]1[CH:24]=[CH:25][C:26]([C:8]([N:4]2[CH2:5][CH2:6][CH2:7][C@H:3]2[C:1]#[N:2])=[O:10])=[CH:30][CH:31]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

8

Reactant 4

HCID 19147p-Octylbenzoic acidHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 6951263tert-butyl (2S)-2-cyanopyrrolidine-1-carboxylate2×

Product 1

HCID 66927397(S)-1-(4-octylbenzoyl)pyrrolidine-2-carbonitrileYield 40%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolvent2×HCID 6422Trifluoroacetic acidSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

General procedure D was used to deprotect 0.4 grams (2.05 mmols) of 28 in 21 mL of dichloromethane and trifluoroacetic acid. After work-up, the TFA salt of 28 was then coupled to 0.6 grams (2.05 mmols) of 4-octylbenzoic acid with 1.1 grams (2.05 mmols) of PyBOP and 1.1 grams (8.2 mmols) of N,N-diisopropylethylamine in 21 mL of dichloromethane according to general procedure E and heating at 50° C. After previously described work-up and purification procedures (column chromatography, 25% EtOAc in hexanes) 0.256 grams (0.82 mmols, 40%) of the title product was recovered.

Sources & evidence

ORD record
ord-1ab72fbfd33a4e6d8b70fd0664be6d3b
Source dataset
uspto-grants-2016_08
Patent number
US09421177B2

Reaction notes

Loading…