Sodium Hydroxide → HCID 71226868, compound

HRID 713408Notes

Reaction equation

HRID 713408 reaction equation
[O:1]=[C:2]1[C:11]2([CH2:16][CH2:15][N:14]([CH2:17][C:18]([O:20]CC)=[O:19])[CH2:13][CH2:12]2)[CH2:10][CH2:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[OH-].[Na+]>CCO>[O:1]=[C:2]1[C:11]2([CH2:12][CH2:13][N:14]([CH2:17][C:18]([OH:20])=[O:19])[CH2:15][CH2:16]2)[CH2:10][CH2:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 71227315HCID 71227315, compound

Product 1

HCID 71226868HCID 71226868, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of ethyl 2-(1-oxo-3,4-dihydro-1H-spiro[naphthalene-2,4′-piperidine]-1′-yl)acetate (71 mg, 0.236 mmol) in EtOH (2 mL) at 25° C. was added NaOH (2 N, 1.39 mL, 2.78 mmol). After being stirred at 25° C. for 16 h, the reaction mixture was extracted with 5 mL of CH2Cl2. The aqueous layer was basified with 2 M HCl to pH 5, and extracted three times with 10 mL of ethyl acetate, dried over Na2SO4 and concentrated. The crude product was purified by flash chromatography (gradient of 100% CH2Cl2 to 90:10 CH2Cl2/ethyl acetate over 20 min) to give the title compound (37 mg, 0.135 mmol). MS calculated for C16H20NO3 274.3. found (ESI) m/z 271.4 (M+H)+, retention time 0.93 min.

Workup

  1. extractionthe reaction mixture was extracted with 5 mL of CH2Cl2
  2. extractionextracted three times with 10 mL of ethyl acetate
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography (gradient of 100% CH2Cl2 to 90:10 CH2Cl2/ethyl acetate over 20 min)

Sources & evidence

ORD record
ord-1953052991724805b419618eba79a30c
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

Loading…