tert-Butyl piperazine-1-carboxylate → HCID 67327082, compound

HRID 1023325Notes

Reaction equation

HRID 1023325 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[N:19]1([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[Si:1]([O:8][CH2:9][CH2:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][N:22]2[CH2:21][CH2:20][N:19]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:24][CH2:23]2)=[CH:13][CH:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 534261684-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]Benzaldehyde

Product 1

HCID 67327082HCID 67327082, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a 1,2-dichloroethane (15 mL) solution of 4-(2-{[tert-butyl(dimethyl)silyl]-oxy}ethyl)benzaldehyde (0.70 g) and tert-butyl piperazine-1-carboxylate (0.52 g) was added NaBH(OAc)3 (0.83 g) at 0° C. The resultant mixture was stirred at room temperature for 66 hours. To the reaction mixture was added saturated aqueous NaHCO3, and extracted with CH2Cl2. The organic layer was washed with saturated aqueous NaCl, dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=9/1 to 2/1) to afford tert-butyl 4-[4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)benzyl]piperazine-1-carboxylate (0.96 g) as a colorless oil.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic layer was washed with saturated aqueous NaCl
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=9/1 to 2/1)

Sources & evidence

ORD record
ord-c6bd434682d8483981fa1e73e1baa3a0
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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