Triethylamine → HCID 18516354、化合物

HRID 1369920ノート

反応式

HRID 1369920 の反応式
[F:1][C:2]12[CH2:14][CH2:13][CH2:12][CH:11]1[C:10]1[CH:9]=[CH:8][C:7]([C:15](O)=[O:16])=[CH:6][C:5]=1[NH:4][C:3]2=[O:18].C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+]>C1COCC1.C(OCC)(=O)C.CO>[F:1][C:2]12[CH2:14][CH2:13][CH2:12][CH:11]1[C:10]1[CH:9]=[CH:8][C:7]([CH2:15][OH:16])=[CH:6][C:5]=1[NH:4][C:3]2=[O:18]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 18516392HCID 18516392、化合物

生成物 1

HCID 18516354HCID 18516354、化合物

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 0.31 g (1.24 mmol) of 3a-fluoro-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one-7-carboxylic acid in 35 ml of THF is treated with 0.20 ml (1.44 mmol) of triethylamine and 0.14 ml (1.44 mmol) of ethyl chloroformate. After 10 minutes at room temperature, 0.14 g (3.72 mmol) of sodium borohydride and, within 15 minutes, 19 ml of methanol, are added to it. After 15 hours, the batch is diluted with ethyl acetate, washed with 20% citric acid, dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography with hexane-ethyl acetate yields 3a-fluoro-7-hydroxymethyl-1,2,3,3a,5,9b-hexahydrocyclo-penta[c]quinolin-4-one, which dissolves in 50 ml of THF and is mixed at 0° C. with 4 portions each of 0.34 ml (2.5 mmol) of triethylamine and 0.19 ml (2.5 mmol) of methanesulfonyl chloride. After the reaction has been completed, the batch is poured onto ice water and extracted with ethyl acetate. The combined extracts are dried (Na2SO4) and concentrated by evaporation in a vacuum. The residue is taken up in 50 ml of 2 M methanolic methylamine solution and refluxed for 4 hours. The volatile components are removed in a vacuum, and the residue is dissolved in 50 ml of dichloromethane. 0.81 g (3.72 mmol) of pyrocarbonic acid-di-tert-butylester is added to it, and after 3 hours, another 0.40 g (1.86 mmol) is added to it. After 2 hours, the batch is diluted with dichloromethane, washed with water, dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography with hexane-ethyl acetate yields 49 mg of product.

後処理

  1. waitAfter 15 hours
  2. washwashed with 20% citric acid
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated by evaporation in a vacuum

出典と根拠

ORDレコード
ord-596eb51b8fc848499eee2697a19dce81
出典データセット
uspto-grants-2003_06
特許番号
US06579883B1

反応ノート

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