Ammonia → (1S,2R)-2-hydroxymethyl-1-cyclopentanecarboxamide

HRID 1416872Notes

Reaction equation

HRID 1416872 reaction equation
[C@H:1]12[CH2:8][O:7][C:6](=[O:9])[C@H:5]1[CH2:4][CH2:3][CH2:2]2.[NH3:10].ClCCl.CO>C(O)C>[OH:7][CH2:8][C@@H:1]1[CH2:2][CH2:3][CH2:4][C@@H:5]1[C:6]([NH2:10])=[O:9]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 11007905HCID 11007905, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 45084199(1S,2R)-2-hydroxymethyl-1-cyclopentanecarboxamideYield 61.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(1R,5S)-(+)-7-oxabicyclo[3.3.0]octan-6-one (1 gram) was dissolved in 5 ml of absolute ethanol, followed by the addition of 0.5 gram of gaseous ammonia. The solution was kept in a stoppered flask, and the progress of the reaction was followed by thin layer chromatography (eluent dichloromethane/methanol 20:1). After the reaction was judged complete, the ethanol was evaporated and the resulting residue redissolved in ethyl acetate. Ammonia was removed by extraction with 1% HCl, and the ethyl acetate solution was dried over MgSO4, filtered, and rotary evaporated to leave 0.7 grams of (1S,2R)-2-hydroxymethyl-1-cydopentanecarboxamide.

Workup

  1. customThe solution was kept in a stoppered flask
  2. customthe ethanol was evaporated
  3. dissolutionthe resulting residue redissolved in ethyl acetate
  4. customAmmonia was removed by extraction with 1% HCl
  5. dry with materialthe ethyl acetate solution was dried over MgSO4
  6. filtrationfiltered
  7. customrotary evaporated

Sources & evidence

ORD record
ord-080d7ea0394f479cb6b02cbaa5e3cbad
Source dataset
uspto-grants-1999_06
Patent number
US05916786

Reaction notes

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