1-Aminocyclopentanemethanol → HCID 10085580, compound

HRID 1293405Notes

Reaction equation

HRID 1293405 reaction equation
Cl[CH2:2][C:3]([N:5]1[C@@H:9]([C:10]#[C:11][CH3:12])[CH2:8][CH2:7][C@H:6]1[C:13]#[N:14])=[O:4].[NH2:15][C:16]1([CH2:21][OH:22])[CH2:20][CH2:19][CH2:18][CH2:17]1>C(#N)C>[OH:22][CH2:21][C:16]1([NH:15][CH2:2][C:3]([N:5]2[C@@H:9]([C:10]#[C:11][CH3:12])[CH2:8][CH2:7][C@H:6]2[C:13]#[N:14])=[O:4])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 663071-AminocyclopentanemethanolHCID 16090855(2S,5R)-1-(Chloroacetyl)-5-(prop-1-yn-1-yl)pyrrolidine-2-carbonitrile

Product 1

HCID 10085580HCID 10085580, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of (2S,5R)-1-(chloroacetyl)-5-propynylpyrrolidine-2-carbonitrile (0.03 g, 0.14 mmol, Example 88D) in acetonitrile (1 mL) at room temperature was added 1-amino-1-cyclopentanemethanol (35 mg, 0.28 mmol). The reaction mixture was stirred at room temperature for 18 hours, concentrated under reduced pressure and purified by flash chromatography with 3% methanol/97% dichloromethane to provide the titled compound. MS (ESI) m/z 290 (M+H)+; 1H NMR (DMSO) δ ppm 4.86 (m, 1H), 4.16 (m, 1H), 3.52 (m, 2H), 3.44 (m, 2H), 2.06-2.39 (m, 4H), 1.96 (m, 2H), 1.86 (d, 3H), 1.75 (m, 6H), 1.56 (m, 2H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by flash chromatography with 3% methanol/97% dichloromethane

Sources & evidence

ORD record
ord-927e91a1f2de46e8b1f3c7d3e597135b
Source dataset
uspto-grants-2007_07
Patent number
US07238724B2

Reaction notes

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