Trifluoroacetic acid → (R)-1-(4-dodecylbenzoyl)pyrrolidine-2-carbonitrile

HRID 1484091Notes

Reaction equation

HRID 1484091 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].FC(F)(F)C(O)=O.[CH2:22]([C:34]1[CH:42]=[CH:41][C:37](C(O)=O)=[CH:36][CH:35]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].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>[CH2:22]([C:34]1[CH:35]=[CH:36][C:37]([C:8]([N:4]2[CH2:5][CH2:6][CH2:7][C@@H:3]2[C:1]#[N:2])=[O:10])=[CH:41][CH:42]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 4133114-Dodecylbenzoic acidHCID 2724699PyBOPHCID 2756788tert-butyl (2R)-2-cyanopyrrolidine-1-carboxylate

Product 1

HCID 53248516(R)-1-(4-dodecylbenzoyl)pyrrolidine-2-carbonitrileYield 39.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

General procedure D was used to deprotect 1.4 mmols of 41 using 14 mL of dichloromethane and trifluoroacetic acid. After previously described recrystallization techniques, the TFA salt of 41 was coupled to 0.4 grams (1.4 mmols) of 4-dodecylbenzoic acid using 0.73 grams (1.4 mmols) of PyBOP and 0.72 grams (5.6 mmols) of N,N-diisopropylethylamine in 14 mL of dichloromethane according to general procedure E. Using previously described work-up and purification techniques (column chromatography, 25% EtOAc in hexanes), yielded 0.2 grams (0.55 mmols, 39%) of the title product as an off-white solid. 1H and 13C NMR data were identical to that of 29.

Workup

  1. customAfter previously described recrystallization techniques
  2. customwork-up and purification techniques (column chromatography, 25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-8578b2e9775f4dc9abbc0d363edf4e0d
Source dataset
uspto-grants-2016_08
Patent number
US09421177B2

Reaction notes

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