Water → HCID 67167753, compound

HRID 84938Notes

Reaction equation

HRID 84938 reaction equation
O=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C@@H:6]2[CH2:13][N:14]([C:16](OC(C)(C)C)=O)[CH2:15][C@H:5]2[CH2:4][NH:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH3:16][N:14]1[CH2:15][C@@H:5]2[C@H:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[CH2:2][NH:3][CH2:4]2)[CH2:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 67167155HCID 67167155, compound

Product 1

HCID 67167753HCID 67167753, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of Example 71A (2.62 g, 8.66 mmol) in tetrahydrofuran (87 mL) was added lithium aluminum hydride in tetrahydrofuran (13.00 mL, 26.0 mmol) in small portions, and the mixture was stirred at room temperature for 24 hours. Water was added carefully and the product was extracted once with dichloromethane, dried over Na2SO4 and concentrated to afford the title compound. 1H NMR (500 MHz, pyridine-d5) δ ppm 7.31 (d, J=7.4, 1H), 7.20-7.17 (m, 2H), 7.13 (d, J=7.7, 1H), 4.58 (dd, J=14.5, 48.4, 2H), 4.01-3.90 (m, 2H), 3.71-3.57 (m, 2H), 3.40 (t, J=10.4, 1H), 3.19-3.05 (m, 2H), 2.71 (s, 3H), 2.66-2.52 (m, 1H); MS (ESI+) m/z 203.0 [M+H]+.

Workup

  1. extractionthe product was extracted once with dichloromethane
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4731ecb25a6b4a6e952eced4398d3978
Source dataset
uspto-grants-2014_09
Patent number
US08846951B2

Reaction notes

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