Potassium Sodium Tartrate → 2',3',5',6'-Tetrahydrospiro[indoline-3,4'-pyran]

HRID 1178913ノート

反応式

HRID 1178913 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].F[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1([C:20]#[N:21])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(COC)OC>[O:17]1[CH2:18][CH2:19][C:14]2([C:9]3[C:10](=[CH:11][CH:12]=[CH:13][CH:8]=3)[NH:21][CH2:20]2)[CH2:15][CH2:16]1

参加物

5

反応物 3

HCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydrideHCID 49875771HCID 49875771、化合物

生成物 1

HCID 589750752',3',5',6'-Tetrahydrospiro[indoline-3,4'-pyran]収率 45.3%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

Add LiAlH4 (398 mg, 10.5 mmol) to a solution of 4-(2-fluoro-phenyl)-tetrahydro-pyran-4-carbonitrile (1.39 g, 6.77 mmol) in dimethoxyethane (25 mL). Stir the solution at reflux overnight then add aq. Satd Rochelle's salt solution (30 mL) and stir for an additional 1 h at RT. Extract the mixture with CH2Cl2 (3×30 mL). Combine the organic extracts and wash with additional aq satd Rochelle's salt solution (30 mL) and brine (30 mL). Dry, filter and concentrate the organic solution then purify the crude material by flash chromatography, using a linear gradient of 100% hexanes and 50% EtOAc/hexanes, to give the title compound (581 mg, 45%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.09 (d, 1H, J=7.3), 7.06 (t, 1H, J=7.6), 6.77 (m, 1H), 6.67 (m, 1H), 3.97 (m, 2H), 3.94 (dt, 2H, J=1.7, 7.9), 3.56 (dt, 2H, J=2.1, 11.8), 3.55 (s, 2H), 1.99 (m, 2H), 1.67 (m, 2H).

後処理

  1. temperatureat reflux overnight
  2. extractionExtract the mixture with CH2Cl2 (3×30 mL)
  3. washCombine the organic extracts and wash with additional
  4. customDry
  5. filtrationfilter
  6. concentrationconcentrate the organic solution
  7. customthen purify the crude material by flash chromatography

出典と根拠

ORDレコード
ord-18453eb1bf5a497097083d0299930bce
出典データセット
uspto-grants-2007_10
特許番号
US07276516B2

反応ノート

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