Acetic Acid → HCID 44242105, compound

HRID 1808139Notes

Reaction equation

HRID 1808139 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@@H:11]([NH2:18])[C:12]2[O:13][C:14]([CH3:17])=[CH:15][N:16]=2)=[CH:2]1.[CH3:19][N:20]([CH3:34])[C:21]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1.C(O)(=O)C>ClCCCl.C(OCC)(=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@@H:11]([NH:18][CH:24]2[CH2:23][CH2:22][C:21]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)([N:20]([CH3:34])[CH3:19])[CH2:26][CH2:25]2)[C:12]2[O:13][C:14]([CH3:17])=[CH:15][N:16]=2)=[CH:2]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 114244924-(Dimethylamino)-4-phenylcyclohexan-1-oneHCID 68794148HCID 68794148, compound

Product 1

HCID 44242105HCID 44242105, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (R)-2-(1H-indol-3-yl)-1-(5-methyloxazol-2-yl)ethylamine (240 mg, 1.0 mmol) and 4-dimethylamino-4-phenylcyclohexanone (218 mg, 1.0 mmol) in 1,2-dichloroethane (15 mL) was mixed with powdered sodium triacetoxyboron hydride (317 mg, 1.5 mmol) and acetic acid (120 mg, 2.0 mmol) and stirred for 18 h at room temperature. The mixture was then diluted with ethyl acetate (80 mL), washed with sodium hydrogencarbonate solution (20 mL) and dried with sodium sulphate. The solvent was removed in a vacuum and the residue purified by flash chromatography (15 g, 12×2.5 cm) with methanol/dichloromethane (1:4).

Workup

  1. washwashed with sodium hydrogencarbonate solution (20 mL)
  2. dry with materialdried with sodium sulphate
  3. customThe solvent was removed in a vacuum
  4. customthe residue purified by flash chromatography (15 g, 12×2.5 cm) with methanol/dichloromethane (1:4)

Sources & evidence

ORD record
ord-7d2b413c4ea141f5bf74ad22526ba76f
Source dataset
uspto-grants-2013_01
Patent number
US08357705B2

Reaction notes

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