Water → (1-hydroxymethyl-cyclopentyl)-carbamic Acid Benzyl Ester

HRID 855865Notes

Reaction equation

HRID 855865 reaction equation
[NH2:1][C:2]1([CH2:7][OH:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.C([O-])(O)=O.[Na+].O.[C:15](=O)([O:24]N1C(=O)CCC1=O)[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O>[CH2:17]([O:16][C:15](=[O:24])[NH:1][C:2]1([CH2:7][OH:8])[CH2:6][CH2:5][CH2:4][CH2:3]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 663071-AminocyclopentanemethanolHCID 83172Benzyl succinimido carbonateHCID 516892Sodium Bicarbonate

Product 1

HCID 11557863(1-hydroxymethyl-cyclopentyl)-carbamic Acid Benzyl Ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 1-amino-1-cyclopentanemethanol (1.15 g, 10 mmol) and NaHCO3 (0.84 g, 10 mmol) in acetone (14 mL)/water (14 ml) at room temperature was added benzyl succinimidyl carbonate (2.5 g, 10 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 (DCI) m/z 250 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-24e100754a684d5ba753b1b0114b6006
Source dataset
uspto-grants-2007_08
Patent number
US07262207B2

Reaction notes

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