Hydrochloric Acid → HCID 59432792, compound

HRID 506859Notes

Reaction equation

HRID 506859 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:8]([CH3:6])[CH2:9][CH2:10][CH3:11])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 59432792HCID 59432792, compoundYield 165.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (100 mg, 0.5 mmol) in MeOH (5 ml) was added NaBH3 CN (32 mg, 0.5 mmol, 1 eq.). The pH of the reaction mixture was adjusted to 5.5 by addition of 5N HCl and stirred for 48 hrs at RT under an inert atmosphere. The solvent was removed under reduced pressure and the crude was taken-up in AcOEt (150 ml). The organic layer was washed with NaHCO3 (10 ml) and with brine (10 ml) and was dried over MgSO4. The solvent was removed under vacuo to give the expected 4-(methyl-propyl-amino)-piperidine-1-carboxylic acid tert-butyl ester (106 mg, 82% yield).

Workup

  1. customThe solvent was removed under reduced pressure
  2. washThe organic layer was washed with NaHCO3 (10 ml) and with brine (10 ml)
  3. dry with materialwas dried over MgSO4
  4. customThe solvent was removed under vacuo

Sources & evidence

ORD record
ord-349cb6417b5f4c0cbf997e910519ea6b
Source dataset
uspto-grants-2010_08
Patent number
US07786121B2

Reaction notes

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