Acetic Anhydride → 1-Acetyl-7-(2-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)ethyl)-6-methoxy-1,2,3,4-tetrahydroquinoline

HRID 494971Notes

Reaction equation

HRID 494971 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[O:8]1[C:12]2([CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]3[CH:29]=[C:28]4[C:23]([CH2:24][CH2:25][CH2:26][NH:27]4)=[CH:22][C:21]=3[O:30][CH3:31])[CH2:14][CH2:13]2)[O:11][CH2:10][CH2:9]1>N1C=CC=CC=1>[C:1]([N:27]1[C:28]2[C:23](=[CH:22][C:21]([O:30][CH3:31])=[C:20]([CH2:19][CH2:18][N:15]3[CH2:14][CH2:13][C:12]4([O:11][CH2:10][CH2:9][O:8]4)[CH2:17][CH2:16]3)[CH:29]=2)[CH2:24][CH2:25][CH2:26]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 576829147-(2-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)ethyl)-6-methoxy-1,2,3,4-tetrahydroquinoline

Product 1

HCID 576828411-Acetyl-7-(2-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)ethyl)-6-methoxy-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3 ml of acetic anhydride and 3 ml of pyridine were added to 251 mg of 7-(2-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)ethyl)-6-methoxy-1,2,3,4-tetrahydroquinoline, and the obtained mixture was then stirred at room temperature for 90 minutes. The reaction solution was concentrated under a reduced pressure. The residue was diluted with ethyl acetate and then washed with water and a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate) and then by silica gel column chromatography (ethyl acetate-methanol), so as to obtain 162 mg of the subject compound.

Workup

  1. concentrationThe reaction solution was concentrated under a reduced pressure
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under a reduced pressure
  6. customThe residue was purified by NH silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-4b3f6052b6a04dfcb9e0f93a6f782b53
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

Loading…