Piperidin-4-ol → [Tert-butoxycarbonylimino-(4-hydroxy-piperidin-1-yl)-methyl]-carbamic acid tert-butyl ester

HRID 251111Notes

Reaction equation

HRID 251111 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:8]([O:12][C:13](=[O:29])[NH:14][C:15](=[N:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])N1C=CC=N1)([CH3:11])([CH3:10])[CH3:9]>C1COCC1>[C:25]([O:24][C:22](=[O:23])[NH:21][C:15](=[N:14][C:13]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:29])[N:5]1[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]1)([CH3:28])([CH3:27])[CH3:26]

Participants

4

Reactant 2

HCID 79341Piperidin-4-olHCID 4428040N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine

Product 1

HCID 67271828[Tert-butoxycarbonylimino-(4-hydroxy-piperidin-1-yl)-methyl]-carbamic acid tert-butyl esterYield 62.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Hydroxypiperidine (0.25 g, 2.5 mmol) and (tert-butoxycarbonylimino-pyrazol-1-yl-methyl)-carbamic acid tert-butyl ester (0.78 g, 2.2 mmol) (Drake, B. et al. Synthesis 1994, 6, 579-582) were dissolved in THF (1 mL) and stirred for 1 hour. The solvent was removed under reduced pressure and EtOAc (20 mL) was added. The organic was washed with an aqueous solution of 15% NaOH (5×15 mL), dried (Na2SO4) and concentrated under reduced pressure to afford [tert-butoxycarbonylimino-(4-hydroxy-piperidin-1-yl)-methyl]-carbamic acid tert-butyl ester as a white solid (0.47 g, 55%).

Workup

  1. customThe solvent was removed under reduced pressure and EtOAc (20 mL)
  2. additionwas added
  3. washThe organic was washed with an aqueous solution of 15% NaOH (5×15 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ee13eef3a06249ff8c064363a7895cda
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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