Lithium Hydroxide → HCID 86585474, compound

HRID 1369236Notes

Reaction equation

HRID 1369236 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]2[CH2:21][CH:20]([CH2:22][C:23](OCC)=O)[C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=3[CH2:17][C:16]=2[CH:32]=1.[Li+].[OH-:34].[CH3:35][C:36]#N.[OH2:38]>C1COCC1.O>[CH2:35]([C:14]1[C:15]2[CH2:21][CH:20]([CH2:22][C:23]([OH:38])=[O:34])[C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=3[CH2:17][C:16]=2[CH:32]=[C:12]([CH2:11][CH2:10][CH2:9][CH2:8][NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH:13]=1)[CH3:36]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 12071468HCID 12071468, compoundHCID 18373917Acetonitrile--water (1/1)

Product 1

HCID 86585474HCID 86585474, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl (±)-10,11-dihydro-3-[4-(pyridin-2-ylamino)-1-butyl]-5H-dibenzo[a,d]cycloheptene-10-acetate (46 mg, 0.11 mmole) and 1.0 N LiOH (0.66 mL, 0.66 mmole) in THF (3 mL) and H2O (3 mL) was stirred at RT. After 24 hr, the reaction mixture was concentrated on the rotavap, and the residue was diluted with H2O (5 mL). The solution was cooled in an ice bath, and 1.0 N AcOH was added slowly to give a white precipitate. Chromatography on C-18 YMC (45% CH3CN/H2O containing 0.1% TFA) gave the title compound (13 mg, 21%) as a white solid: MS (ES) m/e 401.3 (M+H)+. Anal. Calcd for C26H28N2O2.0.75 H2O.1.5 CF3CO2H: C, 59.54; H, 5.31, N, 4.72. Found: C, 59.69; H, 5.31; N, 4.72.

Workup

  1. concentrationthe reaction mixture was concentrated on the rotavap
  2. additionthe residue was diluted with H2O (5 mL)
  3. temperatureThe solution was cooled in an ice bath
  4. addition1.0 N AcOH was added slowly
  5. customto give a white precipitate

Sources & evidence

ORD record
ord-476f4a6832424f928653781d045d06f9
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

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