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

HRID 2360351Notes

Reaction equation

HRID 2360351 reaction equation
[C:1]([CH: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]>>[CH2:15]([C:23]1[CH:24]=[CH:25][C:26]([C:8]([N:4]2[CH2:5][CH2:6][CH2:7][CH: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

3

Reactant 2

HCID 19147p-Octylbenzoic acidHCID 2756786tert-Butyl 2-cyanopyrrolidine-1-carboxylate

Product 1

HCID 669273981-(4-Octylbenzoyl)pyrrolidine-2-carbonitrile

Procedure

General procedure D was used to deprotect 19 (1.2 mmol, 0.24 g). The product was immediately carried on and coupled to 2 (1.2 mmol, 0.281 g) using general procedure F. After standard work up procedures the title product was recovered from flash chromatography to yield 0.238 g (0.76 mmol) after two steps. 1H NMR (500 MHz, CDCl3) δ 7.50 (d, J=8.1, 2H), 7.21 (dd, J=7.9, 14.6, 2H), 4.91 (s, 0.5H), 4.66 (s, 0.5H), 3.67 (s, 1H), 3.56 (s, 1H), 2.66-2.60 (m, 2H), 2.32 (s, 1H), 2.17 (s, 1H), 2.01 (s, 1H), 1.88 (s, OH), 1.60 (d, J=7.5, 2H), 1.28 (dd, J=7.5, 14.4, 10H), 0.87 (t, J=6.8, 3H). 13C NMR (126 MHz, CDCl3) δ 173.09, 146.33, 133.26, 132.60, 128.43, 128.21, 127.64, 127.44, 118.72, 59.24, 52.28, 50.05, 46.85, 35.84, 31.85, 31.19, 29.41, 29.22, 25.42, 22.64, 14.11.

Workup

  1. customAfter standard work up procedures the title product was recovered from flash chromatography
  2. customto yield 0.238 g (0.76 mmol) after two steps

Sources & evidence

ORD record
ord-51e979498aba4f349e74b6f6a13df99f
Source dataset
uspto-grants-2014_04
Patent number
US08686046B2

Reaction notes

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