Hydrochloric Acid → 8-[2-(1,4-Benzodioxan-2-yl)-2-hydroxyethyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one hydrochloride

HRID 1389478ノート

反応式

HRID 1389478 の反応式
[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:4][NH:3][C:2]1=[O:11].[OH:12][CH:13]([CH:16]1[O:21][C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17]1)[CH2:14]Br.C(N(CC)CC)C.[ClH:33]>CO.C(OCC)C.O.CN(C)C=O>[ClH:33].[O:21]1[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17][CH:16]1[CH:13]([OH:12])[CH2:14][N:8]1[CH2:7][CH2:6][C:5]2([O:1][C:2](=[O:11])[NH:3][CH2:4]2)[CH2:10][CH2:9]1

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 126085902-Bromo-1-(2,3-dihydro-1,4-benzodioxin-2-yl)ethan-1-olHCID 129541141-Oxa-3,8-diazaspiro(4.5)decan 2-one

生成物 1

HCID 202966058-[2-(1,4-Benzodioxan-2-yl)-2-hydroxyethyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one hydrochloride

試薬・触媒・溶媒 4

HCID 887Methanol溶媒2 回HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 1.7 g 1-oxa-3,8-diazaspiro[4.5]decan-2-one, 2 g 2-(1-hydroxy-2-bromoethyl)-1,4-benzodioxane [J. Med. Chem., 13, 169 (1970)], 3 ml triethylamine and 5 ml N,N-dimethylformamide is heated at 90° for 18 hours. The mixture is poured into 100 ml water and the resulting mixture stirred for 10 minutes. The stirring is stopped and the aqueous layer decanted. The crude product is filtered through 20 g silica gel with 10% methanol-methylene chloride. Evaporation of the filtrate gives a residue which is taken up in 10 ml methanol. To this solution is added 10 ml of a 3% solution of hydrochloric acid in methanol. Addition of 200 ml of diethyl ether affords a precipitate which is collected by filtration, yielding 1.1 g (mixed erythro and threo) 8-[2-(1,4-benzodioxan-2-yl)-2-hydroxyethyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one hydrochloride, mp 235°-247° (d).

後処理

  1. temperatureis heated at 90° for 18 hours
  2. customthe aqueous layer decanted
  3. filtrationThe crude product is filtered through 20 g silica gel with 10% methanol-methylene chloride
  4. customEvaporation of the filtrate
  5. customgives a residue which
  6. customaffords a precipitate which
  7. filtrationis collected by filtration

出典と根拠

ORDレコード
ord-8a38f49d7b9a4d47a450b8bddbd10c53
出典データセット
uspto-grants-1981_01
特許番号
US04244961

反応ノート

読み込み中…