Ammonia → Cyclohexanecarboxamide, 2-(hydroxymethyl)-, (1S,2R)-(9CI)

HRID 1416871Notes

Reaction equation

HRID 1416871 reaction equation
[C@H:1]12[CH2:9][O:8][C:7](=[O:10])[C@H:6]1[CH2:5][CH2:4][CH2:3][CH2:2]2.[NH3:11].ClCCl.CO>C(O)C>[OH:8][CH2:9][C@@H:1]1[CH2:2][CH2:3][CH2:4][CH2:5][C@@H:6]1[C:7]([NH2:11])=[O:10]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 245563(3Ar,7as)-hexahydro-2-benzofuran-1(3h)-oneHCID 21226129Dichloromethane methanol

Product 1

HCID 14127588Cyclohexanecarboxamide, 2-(hydroxymethyl)-, (1S,2R)-(9CI)Yield 62.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(1R,6S)-(+)-8-oxabicylo[4.3.0]nonan-7-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-cyclohexanecarboxamide.

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-227b51cc1b064f2f988f97a53b38f55f
Source dataset
uspto-grants-1999_06
Patent number
US05916786

Reaction notes

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