Potassium Hydroxide → HCID 67356290, compound

HRID 2387941Notes

Reaction equation

HRID 2387941 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:25][CH2:24][C:11]2([CH2:16][CH2:15][C:14]([OH:23])([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH2:13][CH2:12]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.Cl[CH2:28][CH2:29][N:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1.[OH-].[K+].C1OCCOCCOCCOCCOCCOC1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:25][CH2:24][C:11]2([CH2:12][CH2:13][C:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)([O:23][CH2:28][CH2:29][N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[CH2:15][CH2:16]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 2855718-Crown-6HCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 66755141HCID 66755141, compound

Product 1

HCID 67356290HCID 67356290, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-hydroxy-3-pyridin-3-yl-9-azaspiro[5.5]undecane-9-carboxylic acid tert-butyl ester (0.867 mmol), 1-(2-chloro-ethyl)-pyrrolidine hydrochloride (1.3 mmol, 1.5 equiv.), dry KOH powder (4.33 mmol, 5 equiv.) and catalytic amounts of 18-Crown-6 in toluene (20 ml) was heated for 16 hours at boiling temperature. The reaction mixture was diluted with ethyl acetate (25 ml) and washed with distilled water (10 ml) and saturated sodium chloride solution (10 ml). The organic phase was dried over sodium sulfate and concentrated. The crude product was then purified by column chromatography (5% MeOH in DCM). Yield: 34%

Workup

  1. temperaturewas heated for 16 hours
  2. washwashed with distilled water (10 ml) and saturated sodium chloride solution (10 ml)
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product was then purified by column chromatography (5% MeOH in DCM)

Sources & evidence

ORD record
ord-89f7bf4c7bfe48e29d43c2572763db73
Source dataset
uspto-grants-2012_09
Patent number
US08269000B2

Reaction notes

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