Potassium Carbonate → HCID 24853325, compound

HRID 1015551Notes

Reaction equation

HRID 1015551 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]34[CH2:21][CH:16]5[CH2:17][C:18]([NH2:20])([CH2:19]3)[CH:14]([CH2:15]5)[CH2:13]4)=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[CH:2]1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:29][C:30]([N:32]1[CH2:36][CH2:35][CH2:34][C@H:33]1[C:37]#[N:38])=[O:31]>CS(C)=O.CCOC(C)=O>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([C:12]34[CH2:21][CH:16]5[CH2:17][C:18]([NH:20][CH2:29][C:30]([N:32]6[CH2:36][CH2:35][CH2:34][C@H:33]6[C:37]#[N:38])=[O:31])([CH2:19]3)[CH:14]([CH2:15]5)[CH2:13]4)=[CH:10][CH:11]=2)[CH:5]=[CH:4][CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11073883(2S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrileHCID 59374965HCID 59374965, compound

Product 1

HCID 24853325HCID 24853325, compoundYield 32.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of the compound obtained from step II (0.41 g, 1.5 mmol) and K2CO3 (0.62 g, 4.5 mmol) in DMSO (6 mL) at ice bath temperature under N2 atmosphere was added (S)-1-(2-chloro-acetyl)pyrrolidine-2-carbonitrile (0.26 g, 1.5 mmol). The reaction mixture was gradually warmed to room temperature and stirred for 3 h. Upon completion of the reaction (checked by TLC), the reaction mixture 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-[4-(1H-pyrrol-1-yl)phenyl]hexahydro-2,5-methanopentalen-3a (1H)-yl]glycyl}pyrrolidine-2-carbonitrile as a white solid (0.2 g) in 32% yield as off-white solid. m/z (M+1) 415; 1H NMR (CDCl3) 300 MHz δ 7.38-7.26 (m, 4H), 7.10-7.05 (m, 2H), 6.36-6.32 (m, 2H), 4.84-4.78 (m, 1H), 3.75-3.40 (m, 2H), 3.50 (s, 2H), 2.50-2.42 (m, 1H), 2.38-2.28 (m, 2H), 2.25-2.0 (m, 6H), 2.0-1.70 (m, 7H).

Workup

  1. customUpon completion of the reaction (checked by TLC)
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. customthe solvent was removed under reduced pressure
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-2d01b16cb51a4ae79dc675cb5ed4ac4c
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

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