Sodium Hydroxide → cis-3-Azidomethylcyclopentancarboxylic acid

HRID 2187993Notes

Reaction equation

HRID 2187993 reaction equation
[N:1]([CH2:4][C@@H:5]1[CH2:9][CH2:8][C@H:7]([C:10]([O:12]C)=[O:11])[CH2:6]1)=[N+:2]=[N-:3].[OH-].[Na+]>>[N:1]([CH2:4][C@@H:5]1[CH2:9][CH2:8][C@H:7]([C:10]([OH:12])=[O:11])[CH2:6]1)=[N+:2]=[N-:3]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 86758274Methyl cis-3-azidomethylcyclopentancarboxylate

Product 1

HCID 86758275cis-3-Azidomethylcyclopentancarboxylic acidYield 91%

Procedure

A mixture of methyl cis-3-azidomethylcyclopentancarboxylate (1.2 g, 6.5 mmol) and 1 N sodium hydroxide (12.0 mL, 12 mmol) was stirred at room temperature for about 8 h. The alkaline mixture was extracted with chloroform. The aqueous layer was acidified with hydrochloric acid and extracted twice with chloroform. Combined chloroform extracts from the acidic mixture were dried over sodium sulfate, filtered and concentrated to give about 1.0 g (91%) of cis-3-azidomethylcyclopentancarboxylic acid.

Workup

  1. extractionThe alkaline mixture was extracted with chloroform
  2. extractionextracted twice with chloroform
  3. dry with materialCombined chloroform extracts from the acidic mixture were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3c6b04da23ea4e3a956934210c23a89d
Source dataset
uspto-grants-2002_06
Patent number
US06410594B1

Reaction notes

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