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

HRID 1178913Notes

Reaction equation

HRID 1178913 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-18453eb1bf5a497097083d0299930bce
Source dataset
uspto-grants-2007_10
Patent number
US07276516B2

Reaction notes

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