Acetic Acid → 1,1-Dimethylethyl 4-{4-[3-(methyloxy)-4-nitrophenyl]-3-cyclohexen-1-yl}-1-piperazinecarboxylate

HRID 419405Notes

Reaction equation

HRID 419405 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[CH2:17][CH2:16][C:15](=O)[CH2:14][CH:13]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[C:19]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CC(O)=O>ClCCCl.C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[CH2:17][CH2:16][CH:15]([N:29]3[CH2:28][CH2:27][N:26]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:31][CH2:30]3)[CH2:14][CH:13]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 594528844-[3-(Methyloxy)-4-nitrophenyl]-3-cyclohexen-1-one

Product 1

HCID 594529421,1-Dimethylethyl 4-{4-[3-(methyloxy)-4-nitrophenyl]-3-cyclohexen-1-yl}-1-piperazinecarboxylateYield 77%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 4-[3-(methyloxy)-4-nitrophenyl]-3-cyclohexen-1-one (514 mg, 2.08 mmol) and 1-BOC-piperazine (430 mg, 2.28 mmol) were stirred in DCE (8 mL) at rt under N2. To this mixture was added sodium triacetoxyborohydride (610 mg, 2.89 mmol) and HOAc (125 mg, 2.08 mmol). The reaction was stirred for approximately 24 h. The reaction was diluted with DCM and aqueous (saturated) NaHCO3. The aqueous layer was extracted with DCM (3×). The combined organic layers were dried over MgSO4, filtered, then concentrated and purified by silica gel chromatography to give the title compound of step E (669 mg, 1.60 mmol, 77%) as a tan solid. MS (ESI): 418 [M+H]+.

Workup

  1. extractionThe aqueous layer was extracted with DCM (3×)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-c0d6cf88363540c7bfbe172361d8cbef
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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