(2S,5R)-1-(2-chloroacetyl)-5-ethynylpyrrolidine-2-carbonitrile → HCID 10401914, compound

HRID 1293398Notes

Reaction equation

HRID 1293398 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].[CH3:14][O:15][CH2:16][C:17]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18]1>C(#N)C>[C:10]([C@@H:9]1[N:5]([C:3](=[O:4])[CH2:2][NH:22][C:17]2([CH2:16][O:15][CH3:14])[CH2:21][CH2:20][CH2:19][CH2:18]2)[C@H:6]([C:12]#[N:13])[CH2:7][CH2:8]1)#[CH:11]

Participants

4

Reactant 2

HCID 16090854(2S,5R)-1-(2-chloroacetyl)-5-ethynylpyrrolidine-2-carbonitrileHCID 25220851Cyclopentanamine, 1-(methoxymethyl)- (9CI)

Product 1

HCID 10401914HCID 10401914, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of (2S,5R)-1-(chloroacetyl)-5-ethynylpyrrolidine-2-carbonitrile (0.018 g, 0.09 mmol, Example 8D) in acetonitrile (1 mL) at room temperature was added 1-methoxymethyl-cyclopentylamine (17 mg, 0.13 mmol). The reaction mixture was stirred at room temperature for 18 hours, concentrated under reduced pressure and purified by flash chromatography with 3% methanol:dichloromethane to provide the titled compound. MS (ESI) m/z 290 (M+H)+; 1H NMR (CD3OD) δ 4.84 (m, 2H), 3.48 (m, 2H), 3.41 (s, 3H), 3.31 (m, 2H), 2.43 (d, 1H), 2.30-2.48 (m, 4H), 1.72-1.96 (m, 8H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by flash chromatography with 3% methanol

Sources & evidence

ORD record
ord-5223b5ee375d425193bf837712ed7891
Source dataset
uspto-grants-2007_07
Patent number
US07238724B2

Reaction notes

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