Methyl 4-Boc-piperazine-2-acetate → tert-Butyl 3-(2-hydroxyethyl)piperazine-1-carboxylate

HRID 590556Notes

Reaction equation

HRID 590556 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH:10]([CH2:14][C:15](OC)=[O:16])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[BH4-].[Na+]>CO>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH:10]([CH2:14][CH2:15][OH:16])[CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 2756816Methyl 4-Boc-piperazine-2-acetateHCID 4311764Sodium borohydride

Product 1

HCID 53407692tert-Butyl 3-(2-hydroxyethyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-boc-piperazine-2-acetate (CAS number: 183742-33-8, Chemfinder) (1.0 g, 4 mmol) was dissolved in 10 mL of MeOH, then NaBH4 (1.5 g, 40 mmol) was added portion wise and stirred overnight. The solvent was removed in vacuo and the residue was partitioned between EtOAC and water. The organic layer was separated, and then dried over Na2SO4 and concentrated to give 3-(2-hydroxy-ethyl)-piperazine-1-carboxylic acid tert-butyl ester as crude oil (compound E), which was used directly without further purification.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between EtOAC and water
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1aaa508715b946f0af49589035e71b38
Source dataset
uspto-grants-2016_01
Patent number
US09233978B2

Reaction notes

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