Phthalic Anhydride → (+/-) cis-1-Hydroxymethyl-2-phthalimidocyclopentane

HRID 399043Notes

Reaction equation

HRID 399043 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[CH2:7][OH:8].[C:9]1(=O)[O:14][C:12](=[O:13])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]12>C1(C)C(C)=CC=CC=1>[OH:8][CH2:7][C@@H:3]1[CH2:4][CH2:5][CH2:6][C@@H:2]1[N:1]1[C:12](=[O:13])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]2[C:9]1=[O:14]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 53952592rac-((1R,2S)-2-aminocyclopentyl)methanol

Product 1

HCID 54209124(+/-) cis-1-Hydroxymethyl-2-phthalimidocyclopentaneYield 79.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of (±) cis 1-amino-2-hydroxymethylcyclopentane (0.59 g, 5.1 mmol) and phthalic anhydride (0.76 g, 5.1 mmol) in xylene (40 ml) was heated under argon at reflux using a condenser fitted with a Dean and Stark trap. After 1.5 h the reaction was concentrated in vacuo and the residue was purified by column chromatography on silica gel eluting with diethyl ether to give the title compound as a pale yellow oil (1.0 g).

Workup

  1. temperaturewas heated under argon
  2. temperatureat reflux
  3. customfitted with a Dean and Stark trap
  4. concentrationAfter 1.5 h the reaction was concentrated in vacuo
  5. customthe residue was purified by column chromatography on silica gel eluting with diethyl ether

Sources & evidence

ORD record
ord-ebc97c03a7db465085664fb0ed39915c
Source dataset
uspto-grants-1998_10
Patent number
US05817698

Reaction notes

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