Nitrogen → (8-(4-Chlorophenylsulfonyl)-9-ethyl-1,4-dioxa-8-azaspiro[4.5]decan-7-yl)methyl dimethylcarbamate

HRID 15746

反応式

HRID 15746 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:20]([CH2:21][CH3:22])[CH2:19][C:14]3([O:18][CH2:17][CH2:16][O:15]3)[CH2:13][CH:12]2[CH2:23][OH:24])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.N#N.[CH3:34][N:35]([CH3:39])[C:36](Cl)=[O:37]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:34][N:35]([CH3:39])[C:36](=[O:37])[O:24][CH2:23][CH:12]1[N:11]([S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[CH:20]([CH2:21][CH3:22])[CH2:19][C:14]2([O:18][CH2:17][CH2:16][O:15]2)[CH2:13]1

参加物

7

反応物 4

HCID 947NitrogenHCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 59342380(8-(4-Chlorophenylsulfonyl)-9-ethyl-1,4-dioxa-8-azaspiro[4.5]decan-7-yl)methanol

生成物 1

HCID 59342408(8-(4-Chlorophenylsulfonyl)-9-ethyl-1,4-dioxa-8-azaspiro[4.5]decan-7-yl)methyl dimethylcarbamate収率 136.6%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

(8-(4-Chlorophenylsulfonyl)-9-ethyl-1,4-dioxa-8-azaspiro[4.5]decan-7-yl)methanol (111; 1.19 g, 3.18 mmol) and triethylamine (2.21 ml, 15.9 mmol) were added to CH2Cl2 (15 mL) in a flame-dried flask and placed tinder N2. DMAP (77.8 mg, 0.637 mmol) was added and the mixture stirred for 5 minutes. Dimethylcarbamoyl chloride (0.88 mL, 1.54 mmol) was added dropwise and the reaction stirred for 18 hours. The reaction mixture was concentrated under reduced pressure, and equal portions of EtOAc and water were added. The aqueous layer was extracted with several more portions of EtOAc. The combined organic layers were washed with a dilute NaOH solution, 10% citric acid, brine, dried over Na2SO4 and concentrated to yield 940 mg of 112 as a yellow oil. The material was purified by column chromatography using EtOAc/hexanes gradients to yield 836 mg (59%) of a mixture of cis/trans isomers.

後処理

  1. stirringthe reaction stirred for 18 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and equal portions of EtOAc and water
  3. additionwere added
  4. extractionThe aqueous layer was extracted with several more portions of EtOAc
  5. washThe combined organic layers were washed with a dilute NaOH solution, 10% citric acid, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-2d6a559f17e04d37922fd5bb09eb2b92
出典データセット
uspto-grants-2010_06
特許番号
US07732609B2

関連ノート

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