Potassium Carbonate → HCID 24853122, compound

HRID 1015544Notes

Reaction equation

HRID 1015544 reaction equation
[NH2:1][C:2]12[CH2:9][CH:8]3[CH2:10][C:4]([CH2:11][N:12]4[C:20](=[O:21])[C:19]5[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=5)[C:13]4=[O:22])([CH2:5][CH:6]1[CH2:7]3)[CH2:3]2.C([O-])([O-])=O.[K+].[K+].Cl[CH2:30][C:31]([N:33]1[CH2:37][CH2:36][CH2:35][C@H:34]1[C:38]#[N:39])=[O:32]>CS(C)=O.CCOC(C)=O>[O:21]=[C:20]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=[O:22])[N:12]1[CH2:11][C:4]12[CH2:10][CH:8]3[CH2:9][C:2]([NH:1][CH2:30][C:31]([N:33]4[CH2:37][CH2:36][CH2:35][C@H:34]4[C:38]#[N:39])=[O:32])([CH2:3]1)[CH:6]([CH2:7]3)[CH2:5]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11073883(2S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrileHCID 67017828HCID 67017828, compound

Product 1

HCID 24853122HCID 24853122, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of the compound obtained from step II (0.4 g, 0.98 mmol) and K2CO3 (0.54 g, 3.92 mmol) in DMSO (4.0 mL) at ice bath temperature under nitrogen atmosphere was added (S)-1-(2-chloro-acetyl)pyrrolidine-2-carbonitrile (0.17 g, 1.0 mmol). After stirring the reaction mixture at r.t for 3 h, it was diluted with EtOAc and washed with water and brine, dried over Na2SO4, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography to obtain (2S)-1-{N-[2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]hexahydro-2,5-methanopentalen-3a(1H)-yl]glycyl}pyrrolidine-2-carbonitrile as an off-white solid (0.18 g) in 43% yield. m/z (M+1) 433; 1H NMR (CDCl3) 300 MHz δ 7.90-7.80 (m, 2H), 7.75-7.65 (m, 2-H), 4.86-4.72 (m, 1H), 3.72-3.38 (m, 2H), 3.60 (s, 2H), 3.40 (s, 2H), 2.40-2.05 (m, 7H), 1.90-1.78 (m, 2H), 1.70-1.40 (m, 3H).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. customthe solvent was removed under reduced pressure
  4. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-dcf4a8e93f1142cf889c2e1a48b41dbe
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

Loading…