Cyclopentylamine → (2S,5R)-1-[2-(Cyclopentylamino)acetyl]-5-ethynyl-2-pyrrolidinecarbonitrile

HRID 855870Notes

Reaction equation

HRID 855870 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([NH2:19])[CH2:18][CH2:17][CH2:16][CH2:15]1>C(#N)C>[CH:14]1([NH:19][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])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 16090854(2S,5R)-1-(2-chloroacetyl)-5-ethynylpyrrolidine-2-carbonitrile

Product 1

HCID 10399628(2S,5R)-1-[2-(Cyclopentylamino)acetyl]-5-ethynyl-2-pyrrolidinecarbonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of (2S,5R)-1-(chloroacetyl)-5-ethynylpyrrolidine-2-carbonitrile (0.04 g, 0.203 mmol, Example 8D) in acetonitrile (3 mL) at ambient temperature under nitrogen was added cyclopentylamine (0.04 ml, 0.406 mmol). The reaction mixture was stirred at room temperature 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 (DCI) m/z 246 (M+H)+; 1H NMR (300 MHz, DMSO) δ 1.5-2 (8H, 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-9bad02dd118041e1953cc58607542ab8
Source dataset
uspto-grants-2007_08
Patent number
US07262207B2

Reaction notes

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