(S)-2-(3-Carboxypropyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester → (S)-2-(4-Hydroxybutyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester

HRID 131412Notes

Reaction equation

HRID 131412 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C@@H:9]1[CH2:21][CH2:22][CH2:23][C:24](O)=[O:25])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:10][C@@H:9]1[CH2:21][CH2:22][CH2:23][CH2:24][OH:25])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 58625921(S)-2-(3-Carboxypropyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester

Product 1

HCID 58626015(S)-2-(4-Hydroxybutyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Into a stirred solution of (S)-2-(3-carboxypropyl)-piperazine-1,4-dicarboxylic acid di-tert-butyl ester (0.596 g, 1.60 mmol) in THF add 1.0 M BH3 in THF (3.2 mL, 3.20 mmol) and continue stirring overnight. Concentrate the mixture under reduced pressure, dilute with H2O (30 mL) and extract with EtOAc (3×50 mL). Dry the organic layers with Na2SO4 filter concentrate under reduced pressure, azeotrope the residue with CH2Cl2/hexanes (1:2) and place the residue under vacuum to give the title compound: colorless solid (0.604 g), mass spectrum (m/e):359.12 (M+H).

Workup

  1. concentrationConcentrate the mixture under reduced pressure
  2. additiondilute with H2O (30 mL)
  3. extractionextract with EtOAc (3×50 mL)
  4. dry with materialDry the organic layers with Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-a119efaac9a64f28944b4ec119f20da3
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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