Cyclopropylamine → HCID 10262802, compound

HRID 855890Notes

Reaction equation

HRID 855890 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].[CH:14]1([NH2:17])[CH2:16][CH2:15]1>C(#N)C>[CH:14]1([NH:17][CH2:2][C:3]([N:5]2[C@@H:9]([C:10]#[CH:11])[CH2:8][CH2:7][C@H:6]2[C:12]#[N:13])=[O:4])[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 16090854(2S,5R)-1-(2-chloroacetyl)-5-ethynylpyrrolidine-2-carbonitrile

Product 1

HCID 10262802HCID 10262802, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of Example 8D (0.045 g, 0.228 mmol) in acetonitrile (2 mL) at room temperature under nitrogen was added cyclopropylamine (0.032 ml, 0.457 mmol). The reaction mixture was stirred overnight and then concentrated under reduced pressure. The residue was flash chromatographed with 3% MeOH/CH2Cl2 to provide the desired compound as a pale yellow oil. MS m/z 218 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 1.5-2 (4H, 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).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customchromatographed with 3% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-8131499ac99c4a56951d785438fb07d3
Source dataset
uspto-grants-2007_08
Patent number
US07262207B2

Reaction notes

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