tert-Butyl piperazine-1-carboxylate → HCID 89838174, compound

HRID 1771143Notes

Reaction equation

HRID 1771143 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].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([O:27][CH3:28])[C:23]=1[O:24][CH2:25][CH3:26])[CH:19]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C([O-])(O)=O.[Na+]>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][N:11]([CH2:19][C:18]2[CH:21]=[C:22]([O:27][CH3:28])[C:23]([O:24][CH2:25][CH3:26])=[C:16]([O:15][CH3:14])[CH:17]=2)[CH2:12][CH2:13]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 4771099HCID 4771099, compoundHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 89838174HCID 89838174, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
20 °C

Procedure

The synthesis is carried out in argon condition. 2.2 g (11.8 mmol) of N-Boc-piperazine and 2.5 g (11.8 mmol) of 3,5-dimethoxy-4-ethoxybenzaldehyde are mixed in 50 ml of dry of dichloromethane. After dissolution 2 drops of acetic acid is added, then 4.25 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, concentrated in vacuum at 50÷80° C. The residue (4.1 g of oil) is used on the next step.

Workup

  1. dry with materialof dry of dichloromethane
  2. dissolutionAfter dissolution 2 drops of acetic acid
  3. additionis added
  4. customThe organic layer is separated
  5. washwashed with 5% Na2CO3 solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered off
  8. concentrationconcentrated in vacuum at 50÷80° C

Sources & evidence

ORD record
ord-6b917e080bec4743a2d3eccbad82cd91
Source dataset
uspto-grants-2016_02
Patent number
US09249115B2

Reaction notes

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