Acetic Acid → tert-Butyl (1-isopropylpiperidin-4-yl)carbamate

HRID 2250424Notes

Reaction equation

HRID 2250424 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:15](O)(=O)[CH3:16].[CH3:19]O>CC(C)=O>[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH:15]([CH3:16])[CH3:19])[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 20801240tert-Butyl (1-isopropylpiperidin-4-yl)carbamate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5.0 g Piperidin-4-yl-carbamic acid tert-butyl ester in 15 mL methanol, 7.34 mL acetone, 3.14 g Na(CN)BH3 and 0.3 mL acetic acid were added. After stirring for 16 h at RT the solvent was removed under reduced pressure and the residue was partitioned between 30 mL of water and 30 mL of ethyl acetate. The organic layer was washed with saturated Na2CO3 solution, water and then dried over Na2SO4. Following filtration, the solvent was removed under reduced pressure to yields a white solid. Yield: 4.8 g MS (ES+): m/e=243.

Workup

  1. customwas removed under reduced pressure
  2. customthe residue was partitioned between 30 mL of water and 30 mL of ethyl acetate
  3. washThe organic layer was washed with saturated Na2CO3 solution, water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltration
  6. customthe solvent was removed under reduced pressure
  7. customto yields a white solid

Sources & evidence

ORD record
ord-0212c9f183c741feaa5a8ac643d1e11e
Source dataset
uspto-grants-2008_01
Patent number
US07317027B2

Reaction notes

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