tert-Butyl 4-oxopiperidine-1-carboxylate → 5-fluoro-1-(piperidin-4-yl)-2,3-dihydro-1H-indole

HRID 45583

反応式

HRID 45583 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2.C([N:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1)(OC(C)(C)C)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O.C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:21]1[CH2:22][CH2:23][NH:18][CH2:19][CH2:20]1)[CH2:6][CH2:5]2

参加物

7

反応物 4

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 27744635-FluoroindolineHCID 5049666Sodium triacetoxyborohydrideHCID 86585896Sodium bicarbonate water

生成物 1

HCID 674178425-fluoro-1-(piperidin-4-yl)-2,3-dihydro-1H-indole

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 5-fluoroindoline (1.0 g, 7.30 mmol) and N-Boc-4-piperidone (1.60 g, 7.50 mmol) in tetrahydrofuran (10.0 mL) was added sodium triacetoxyborohydride (1.80 g, 7.50 mmol). After stirring for 3 hours at room temperature, to the mixture were added saturated sodium bicarbonate water and ethyl acetate, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified with silica gel column (chloroform/methanol=98/2 to 90/10) to give a Boc derivative of the title compound. MS (ESI+) 321 (M++1, 100%)

後処理

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified with silica gel column (chloroform/methanol=98/2 to 90/10)

出典と根拠

ORDレコード
ord-e200522c45314eee9bac792acc4c12d9
出典データセット
uspto-grants-2013_09
特許番号
US08541585B2

関連ノート

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