Potassium Sodium Tartrate → Spiro[cyclobutane-1,3'-indoline]

HRID 736978ノート

反応式

HRID 736978 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]OC[CH2:15]1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(COC)OC>[NH:21]1[C:8]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:14]2([CH2:15][CH2:18][CH2:19]2)[CH2:20]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 27274706Spiro[cyclobutane-1,3'-indoline]収率 10.2%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

Add LiAlH4 (266 mg, 7.01 mmol) to a solution of 4-(2-fluoro-phenyl)-tetrahydro-pyran-4-carbonitrile (488 mg, 2.72 mmol) in dimethoxyethane (30 mL). Stir the solution at reflux for 4d, then add aq. Satd Rochelle's salt solution (30 mL) and stir for an additional 1 h at RT. Extract the mixture with Et2O (3×30 mL). Combine the organic extracts and wash with 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 to 30% EtOAc/hexanes, to give the title compound (44 mg, 10%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.31 (m, 1H), 7.03 (dt, 1H, J=1.4, 7.5), 6.79 (dt, 1H, J=0.9, 7.5), 6.64 (d, 1H, J=7.9), 2.36 (m, 2H), 2.21 (m, 2H), 2.02 (m, 2H).

後処理

  1. extractionExtract the mixture with Et2O (3×30 mL)
  2. washCombine the organic extracts and wash with brine (30 mL)
  3. customDry
  4. filtrationfilter
  5. concentrationconcentrate the organic solution
  6. customthen purify the crude material by flash chromatography

出典と根拠

ORDレコード
ord-18f89183ce0141799af9704149dc9492
出典データセット
uspto-grants-2009_09
特許番号
US07595339B2

反応ノート

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