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

HRID 1178913노트

반응식

HRID 1178913 반응식
[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

참가 물질

5

반응물 3

HCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydrideHCID 49875771HCID 49875771, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-18453eb1bf5a497097083d0299930bce
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07276516B2

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