Ammonia → HCID 14986682, compound

HRID 465586Notes

Reaction equation

HRID 465586 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][CH2:10][C:11]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:15][CH2:14][CH2:13][C:12]1=[O:16].[NH3:22]>C(O)C>[CH2:20]([O:19][C:17]([CH:11]([CH2:10][CH2:9][CH2:8][O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)[CH2:15][CH2:14][CH2:13][C:12]([NH2:22])=[O:16])=[O:18])[CH3:21]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 19874793HCID 19874793, compound

Product 1

HCID 14986682HCID 14986682, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.5 g (1.67 mmol) 2-[3-(tetrahydropyranyloxy)propyl]-2-ethoxycarbonylcyclopentanone and 5 ml ethanol is saturated with ammonia gas at 5° in a thick-wall tube. The tube is sealed and heated to 80° for 17 h. The reaction mixture is cooled and then subjected to evaporation. The resulting oil is chromatographed using 4:1 ethylacetate/hexane +1% aqueous ammonia to yield 5-ethoxycarbonyl-5-[3-(tetrahydropyranyloxy)propyl]-valeramide; IR (neat): 3413, 3349, 1727, 1668 cm-1.

Workup

  1. customThe tube is sealed
  2. temperatureheated to 80° for 17 h
  3. temperatureThe reaction mixture is cooled
  4. customsubjected to evaporation
  5. customThe resulting oil is chromatographed

Sources & evidence

ORD record
ord-33d762fa37234a4bb160e5149ec2482c
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

Loading…