1-Aminocyclopentanemethanol → HCID 10333612, compound

HRID 1293401Notes

Reaction equation

HRID 1293401 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].[NH2:14][C:15]1([CH2:20][OH:21])[CH2:19][CH2:18][CH2:17][CH2:16]1>C(#N)C>[C:10]([C@@H:9]1[N:5]([C:3](=[O:4])[CH2:2][NH:14][C:15]2([CH2:20][OH:21])[CH2:19][CH2:18][CH2:17][CH2:16]2)[C@H:6]([C:12]#[N:13])[CH2:7][CH2:8]1)#[CH:11]

Participants

4

Reactant 2

HCID 663071-AminocyclopentanemethanolHCID 16090854(2S,5R)-1-(2-chloroacetyl)-5-ethynylpyrrolidine-2-carbonitrile

Product 1

HCID 10333612HCID 10333612, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of (2S,5R)-1-(chloroacetyl)-5-ethynylpyrrolidine-2-carbonitrile (0.030 g, 0.15 mmol, Example 8D) in acetonitrile (1 mL) at room temperature was added 1-amino-1-cyclopentanemethanol (35 mg, 0.31 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 276 (M+H)+; 1H NMR (DMSO) δ 4.99 (m, 1H), 4.86 (t, 1H), 4.28 (m, 1H), 4.00 (m, 1H), 3.50 (d, 2H), 3.51 (m, 2H), 2.27 (m, 2H), 2.14 (m, 1H), 1.75 (m, 6H), 1.55 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-ea76a2de24394ec187c062b4e7917038
Source dataset
uspto-grants-2007_07
Patent number
US07238724B2

Reaction notes

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