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

HRID 1293395Notes

Reaction equation

HRID 1293395 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-7bd1cdeb45cc49b3807d099c11b21d4a
Source dataset
uspto-grants-2007_07
Patent number
US07238724B2

Reaction notes

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