Potassium Carbonate → HCID 86600842, compound

HRID 855892Notes

Reaction equation

HRID 855892 reaction equation
Cl[CH2:2][C:3]([N:5]1[C@@H:9]([C:10]#[CH:11])[CH2:8][CH2:7][C@H:6]1[C:12]#[N:13])=[O:4].[C:14](=[O:17])([O-])[O-].[K+].[K+]>C(#N)C>[C:10]([C@@H:9]1[N:5]([C:3](=[O:4])[CH2:2][NH:5][C@@H:6]2[CH2:12][CH2:14][O:17][CH2:7]2)[C@H:6]([C:12]#[N:13])[CH2:7][CH2:8]1)#[CH:11]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 16090854(2S,5R)-1-(2-chloroacetyl)-5-ethynylpyrrolidine-2-carbonitrile

Product 1

HCID 86600842HCID 86600842, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of Example 8D (0.03 g, 0.153 mmol) and potassium carbonate (0.2 g, 1.53 mmol) in acetonitrile (2 mL), at room temperature under nitrogen was added R(+)-3-aminotetrahydrofuran toluene-4-sulfonate (0.08 g, 0.32 mmol). The reaction mixture was stirred overnight and then concentrated under reduced pressure. The residue was flash chromatographed with 2% MeOH/CH2Cl2 to provide the desired compound as a pale yellow oil. MS (DCI) m/z 248 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 1.5-2 (2H, m), 2.11-2.21 (2H, m), 2.45-2.48 (2H, m), 3.78 (1H, d), 3.8-4.5 (2H, m), 4.53-4.55 (1H, t), 5.01 (1H, m), 5.05 (1H, m), 5.43-5.9 (4H, m).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customchromatographed with 2% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-5d7e128bfe6940f39b42cf07003b4ff4
Source dataset
uspto-grants-2007_08
Patent number
US07262207B2

Reaction notes

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