Methanol → HCID 67001762, compound

HRID 1186242Notes

Reaction equation

HRID 1186242 reaction equation
CN(CC)C.O=[C:7]1[NH:13][C:12]2[CH:14]=[CH:15][CH:16]=[N:17][C:11]=2[N:10]2[CH2:18][CH2:19][N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:21][CH:9]2[CH2:8]1.CO.[OH-].[Na+]>O1CCCC1.O>[N:17]1[C:11]2[N:10]3[CH2:18][CH2:19][N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:21][CH:9]3[CH2:8][CH2:7][NH:13][C:12]=2[CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 11723Dimethylethylamine2×HCID 14798Sodium HydroxideHCID 67001482HCID 67001482, compound

Product 1

HCID 67001762HCID 67001762, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of alane-N,N-dimethylethylamine complex (0.5 M in toluene, 5.0 mL, 2.50 mmol) was added dropwise over 2 minutes to a solution of the product of Example 64A (506 mg, 1.59 mmol) in dry tetrahydrofuran (22 mL). The reaction was stirred at room temperature for 5 hours. Additional portions of alane-N,N-dimethylethylamine complex (0.5 M in toluene, 5.0 mL, 2.50 mmol) were added after 1 hour, and again after 4 hours. Methanol (10 mL) was added, followed after 10 minutes by water (20 mL) and 25% NaOH (3 mL). The mixture was stirred for 10 minutes, and the aqueous layer was separated and extracted with ethyl acetate (30 mL). The combined organic phases were washed with brine, dried (Na2SO4) and concentrated under vacuum. The residue was purified by chromatography (SiO2, eluted with ethyl acetate-ethanol, 90:10) to provide the title compound: 1H NMR (300 MHz, CDCl3) δ ppm 1.48 (s, 9H), 1.73-1.88 (m, 1H), 1.90-2.07 (m, 1H), 3.17-3.40 (m, 2H), 3.40-3.83 (m, 7H), 6.67 (dd, J=7.8, 4.8 Hz, 1H), 6.76 (d, J=7.8 Hz, 1H), 7.75 (dd, J=4.7, 1.7 Hz, 1H); MS (DCI) m/z 305 (M+H)+.

Workup

  1. waitagain after 4 hours
  2. stirringThe mixture was stirred for 10 minutes
  3. customthe aqueous layer was separated
  4. extractionextracted with ethyl acetate (30 mL)
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by chromatography (SiO2, eluted with ethyl acetate-ethanol, 90:10)

Sources & evidence

ORD record
ord-4cb0ba8cd7844a00978a9a0c6def01df
Source dataset
uspto-grants-2014_03
Patent number
US08673896B2

Reaction notes

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