Acetic Acid → HCID 68769376, compound

HRID 2382205Notes

Reaction equation

HRID 2382205 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([N:14]3[CH2:19][CH2:18][NH:17][C@H:16]([CH3:20])[CH2:15]3)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:21]([O:25][CH3:26])(=[O:24])[CH:22]=O.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCl.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([N:14]3[CH2:19][CH2:18][N:17]([CH2:22][C:21]([O:25][CH3:26])=[O:24])[C@H:16]([CH3:20])[CH2:15]3)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 70205Acetic acid, 2-oxo-, methyl esterHCID 5049666Sodium triacetoxyborohydrideHCID 68758453HCID 68758453, compound

Product 1

HCID 68769376HCID 68769376, compoundYield 65.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-1-(1-(4-chlorophenyl)cyclohexyl)-3-methylpiperazine (0.6 g, 2.05 mmol) in dichloromethane at room temperature were added methyl glyoxalate (0.23 g, 2.61 mmol), acetic acid (0.18 g, 3 mmol) and Na(OAc)3BH (1.08 g, 5.1 mmol). The reaction mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the crude product. It was purified by silica gel (100-200 mesh) column chromatography eluting with ethyl acetate in n-hexanes to afford 0.49 g of (R)-methyl 2-(4-(1-(4-chlorophenyl)cyclohexyl)-2-methyl-piperazin-1-yl)acetate.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto afford the crude product
  5. customIt was purified by silica gel (100-200 mesh) column chromatography
  6. washeluting with ethyl acetate in n-hexanes

Sources & evidence

ORD record
ord-c6b6c2b8685f41b1854cf517d5fb3d56
Source dataset
uspto-grants-2012_09
Patent number
US08258306B2

Reaction notes

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