tert-Butyl piperazine-1-carboxylate → HCID 89838245, compound

HRID 1771140Notes

Reaction equation

HRID 1771140 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:14]([C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[CH:21]=O)([CH3:17])([CH3:16])[CH3:15].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCl.C(O)(=O)C>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][N:11]([CH2:21][C:20]2[CH:23]=[CH:24][C:25]([O:26][CH3:27])=[C:18]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:19]=2)[CH2:12][CH2:13]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

7

Reactant 4

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 516892Sodium BicarbonateHCID 37746043-tert-butyl-4-methoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 89838245HCID 89838245, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

The synthesis is carried out in argon condition. 2 g (10.7 mmol) of N-Boc-piperazine and 2.06 g (10.7 mmol) of 3-tert-butyl-4-methoxybenzaldehyde are mixed in 30 ml of dry dichloromethane. After dissolution 2 drops of acetic acid is added, then 4.24 g (20 mmol) of NaBH(OAc)3 is added and the mixture is stirred for 12 h at 20° C. Then 20 ml of 5% NaHCO3 aqueous solution is added dropwise with care to the reaction mixture. The organic layer is separated, washed with 5% Na2CO3 solution, dried over sodium sulfate, filtered off and concentrated in vacuum at 50÷80° C. The residue (3.5 g of yellow oil) is used on the next step.

Workup

  1. additionis added
  2. customThe organic layer is separated
  3. washwashed with 5% Na2CO3 solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered off
  6. concentrationconcentrated in vacuum at 50÷80° C

Sources & evidence

ORD record
ord-ca309766a7ba40cb872c77b83d3d0e2f
Source dataset
uspto-grants-2016_02
Patent number
US09249115B2

Reaction notes

Loading…