Lithium Hydroxide → N-1-Boc-Amino-3-cyclopentene

HRID 1693343Notes

Reaction equation

HRID 1693343 reaction equation
C(OC(=O)C([N:7]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:8]1[CH2:12][CH:11]=[CH:10][CH2:9]1)=O)C.[Li+].[OH-]>C1COCC1.O>[C:16]([O:15][C:13](=[O:14])[NH:7][CH:8]1[CH2:9][CH:10]=[CH:11][CH2:12]1)([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59858014(Tert-butoxycarbonyl-cyclopent-3-enyl-amino)-oxo-acetic acid ethyl ester

Product 1

HCID 2756764N-1-Boc-Amino-3-cyclopenteneYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution cooled in an ice-water bath of the above crude product, (tert-butoxycarbonyl-cyclopent-3-enyl-amino)-oxo-acetic acid ethyl ester, (3.80 g) in THF (35 mL) was added a solution of LiOH (0.0765 mol) in water (35 mL). The mixture was stirred in the ice-water bath for 3 h. The organic material was extracted with CH2Cl2 (30 mL×3), the organic layers were combined and washed with brine (30 mL×2), and the solvent was removed in vacuo. The residue was purified by column chromatography (silica gel, 100% dichloromethane) to obtain white crystals of pure product (53%).

Workup

  1. extractionThe organic material was extracted with CH2Cl2 (30 mL×3)
  2. washwashed with brine (30 mL×2)
  3. customthe solvent was removed in vacuo
  4. customThe residue was purified by column chromatography (silica gel, 100% dichloromethane)

Sources & evidence

ORD record
ord-1ef55da84ab746239435d0c2216d5e50
Source dataset
uspto-grants-2012_04
Patent number
US08158658B2

Reaction notes

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