Triethylamine → 7-(2,4-Dimethoxy-benzyl)-2-oxa-7-aza-spiro[3.5]nonane

HRID 1850311Notes

Reaction equation

HRID 1850311 reaction equation
CS(O[CH2:6][CH2:7][C:8]1([CH2:12][CH2:13]OS(C)(=O)=O)[CH2:11][O:10][CH2:9]1)(=O)=O.[CH3:19][O:20][C:21]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:22]=1[CH2:23][NH2:24].CCN(CC)CC>CC#N>[CH3:19][O:20][C:21]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:22]=1[CH2:23][N:24]1[CH2:6][CH2:7][C:8]2([CH2:9][O:10][CH2:11]2)[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5972502,4-DimethoxybenzylamineHCID 86660168Methanesulfonic acid 2-[3-(2-methanesulfonyloxy-ethyl)-oxetan-3-YL]-ethyl ester

Product 1

HCID 674692077-(2,4-Dimethoxy-benzyl)-2-oxa-7-aza-spiro[3.5]nonaneYield 65.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (124) (2.0 g, 6.6 mmol) in MeCN (20 mL) were added 2,4-dimethoxy-benzylamine (1.2 g, 7.3 mmol) and Et3N (2.0 g, 19.8 mmol). The solution was allowed to heat at reflux for 12 h. The reaction mixture was then filtered through a pad of silica (washing with 30 percent EtOAc:Petrol ether), and the solvent removed under reduced pressure to give the product (125) (1.2 g, 4.3 mmol, yield: 65%). ESI-MS (M+1): 278 calc. for C16H23NO3 277.

Workup

  1. temperatureto heat
  2. temperatureat reflux for 12 h
  3. filtrationThe reaction mixture was then filtered through a pad of silica (washing with 30 percent EtOAc:Petrol ether)
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-5f51d0ad5cac4a12b73c10b6d0de1304
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

Loading…