Sodium Acetate → HCID 67389047, compound

HRID 1929399Notes

Reaction equation

HRID 1929399 reaction equation
Cl.[CH:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH:3]1[CH2:12][NH2:13])[CH2:9]2.[CH3:14][C:15]1([CH3:40])[CH2:20][CH:19]([CH2:21][N:22]2[CH2:27][CH2:26][N:25]([C:28]3[CH:38]=[CH:37][C:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:30][CH:29]=3)[CH2:24][CH2:23]2)[C:18](=O)[CH2:17][CH2:16]1.C([O-])(=O)C.[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH:3]1[CH2:12][NH:13][CH:18]1[CH2:17][CH2:16][C:15]([CH3:40])([CH3:14])[CH2:20][CH:19]1[CH2:21][N:22]1[CH2:23][CH2:24][N:25]([C:28]3[CH:38]=[CH:37][C:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:30][CH:29]=3)[CH2:26][CH2:27]1)[CH2:9]2

Participants

6

Reactant 4

HCID 517045Sodium AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 127014531-(Tricyclo[3.3.1.1~3,7~]decan-2-yl)methanamine--hydrogen chloride (1/1)HCID 57474949HCID 57474949, compound

Product 1

HCID 67389047HCID 67389047, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

(2-Adamantylmethyl)amine hydrochloride salt (195 mg), ethyl 4-(4-((5,5-dimethyl-2-oxocyclohexyl)methyl)piperazin-1-yl)benzoate (200 mg) and sodium acetate (44 mg) were suspended in anhydrous dichloroethane. The reaction mixture was stirred at room temperature for 20 minutes, followed by the addition of sodium triacetoxyborohydride (228 mg). The reaction mixture was stirred at room temperature overnight. The reaction was quenched with saturated NaHCO3 aqueous solution. The reaction mixture was extracted with ethyl acetate, and washed with water and brine. The organic phase was dried over Na2SO4, filtered, and concentrated. The residue was purified by flash column purification with 0-5% methanol/dichloromethane to afford the title compound.

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. customThe reaction was quenched with saturated NaHCO3 aqueous solution
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash column purification with 0-5% methanol/dichloromethane

Sources & evidence

ORD record
ord-694deed0f6e148f0b9442a599fbe8439
Source dataset
uspto-grants-2012_05
Patent number
US08188077B2

Reaction notes

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