Sodium Hydroxide → HCID 5273765, compound

HRID 1063390Notes

Reaction equation

HRID 1063390 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][C:6]1([CH2:22][CH2:23][CH3:24])[C:11]2[NH:12][C:13]3[C:18]([C:10]=2[CH2:9][CH2:8][O:7]1)=[C:17]([C:19]#[N:20])[CH:16]=[CH:15][C:14]=3[CH3:21])C.[OH-].[Na+]>C1COCC1.CO>[C:19]([C:17]1[CH:16]=[CH:15][C:14]([CH3:21])=[C:13]2[C:18]=1[C:10]1[CH2:9][CH2:8][O:7][C:6]([CH2:22][CH2:23][CH3:24])([CH2:5][C:4]([OH:25])=[O:3])[C:11]=1[NH:12]2)#[N:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 5273764HCID 5273764, compound

Product 1

HCID 5273765HCID 5273765, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 5-cyano-8-methyl-1-propyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid ethyl ester (0.959 g, 2.82 mmol) in THF/MeOH (7 mL/15 mL) was added 1 N NaOH (5.64 mL, 5.64 mmol). The reaction mixture was stirred at ambient temperature overnight. Most of THF/MeOH was removed under reduced pressure and the resulting mixture was acidified with 1 N HCl. The mixture was extracted with EtOAc (3×30 mL). The combined organic phase was washed with brine (60 mL), dried over Na2SO4 and concentrated to provide 0.868 g (99%) of title compound as a white solid. 1H NMR (acetone-d6): 300 MHz δ 10.37 (bs, 1H), 7.35 (d, J=7.50 Hz, 1H), 7.03 (d, J=7.50 Hz, 1H), 4.05 (m, 2H), 3.08-2.91 (m, 4H), 2.54 (s, 3H), 2.09 (m, 2H), 1.45 (m, 1H), 1.03 (m, 1H), 0.84 (t, J=7.26 Hz, 3H).

Workup

  1. customMost of THF/MeOH was removed under reduced pressure
  2. extractionThe mixture was extracted with EtOAc (3×30 mL)
  3. washThe combined organic phase was washed with brine (60 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1fff7cb55f47478a998728e243d489e0
Source dataset
uspto-grants-2005_11
Patent number
US06964979B2

Reaction notes

Loading…