Sodium Hydroxide → HCID 16042340, compound

HRID 2218287Notes

Reaction equation

HRID 2218287 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[C:8]([O:13][CH3:14])[CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([C:15]([N:17]2[CH2:22][CH2:21][C:20]3([CH2:31][C:30](=[O:32])[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([C:33]([O:35]CC5C=CC=CC=5)=[O:34])[CH:28]=4)[O:23]3)[CH2:19][CH2:18]2)=[O:16])[CH:4]=1.[OH-].[Na+]>C1COCC1.CO.[Pd]>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[C:8]([O:13][CH3:14])[CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([C:15]([N:17]2[CH2:22][CH2:21][C:20]3([CH2:31][C:30](=[O:32])[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([C:33]([OH:35])=[O:34])[CH:28]=4)[O:23]3)[CH2:19][CH2:18]2)=[O:16])[CH:4]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 16042339HCID 16042339, compound

Product 1

HCID 16042340HCID 16042340, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1′-[(4,8-Dimethoxyquinolin-2-yl)carbonyl]-6-(benzyloxycarbonyl)-spiro[chroman-2,4′-piperidin]-4-one (680 mg) was dissolved in 10 mL of THF and 10 mL of methanol, and vigorously stirred on 10% Pd/C under a hydrogen atmosphere for 21 hours. 1.2 mL of 1N NaOH was added to it, and filtered through Celite, and the filtrate was concentrated. 20 mL of water was added to the residue, and extracted with ethyl acetate (3×20 mL). The aqueous layer was acidified with 1N HCl, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate, and concentrated to obtain the intended compound. 1H-NMR (DMSO-d6) δ: 8.30 (1H, d, J=2.2 Hz), 8.11(1H, dd, J=8.7, 2.2 Hz), 7.68 (1H, dd, J=8.3, 1.2 Hz), 7.52 (1H, dd, J=8.3, 7.7 Hz), 7.23 (1H, dd, J=1.2, 7.7 Hz), 7.21 (1H, d, J=8.7 Hz), 7.18 (1H, s), 4.35-4.28 (1H, m), 4.07 (3H, s), 3.94 (3H, s), 3.69-3.62 (1H, m), 3.50-3.22 (2H, m), 2.97 (2H, s), 2.12-2.04 (1H, m), 1.96-1.80 (3H, m). MS [M+H]+=477.

Workup

  1. filtrationfiltered through Celite
  2. concentrationthe filtrate was concentrated
  3. addition20 mL of water was added to the residue
  4. extractionextracted with ethyl acetate (3×20 mL)
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customto obtain the intended compound

Sources & evidence

ORD record
ord-1371cfd33f0c478bb1649d2a4e7f9e84
Source dataset
uspto-grants-2008_08
Patent number
US07410976B2

Reaction notes

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