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

HRID 900230Notes

Reaction equation

HRID 900230 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>>[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

4

Reactant 3

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

Product 1

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

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 and the residue was partitioned between 30 ml of water and 30 ml ethylacetate. The organic layer was washed with saturated Na2CO3 solution, water and then dried over Na2SO4. The solvent was removed under reduced pressure and yields a white solid.

Workup

  1. customwas removed
  2. customthe residue was partitioned between 30 ml of water and 30 ml ethylacetate
  3. washThe organic layer was washed with saturated Na2CO3 solution, water
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customyields a white solid

Sources & evidence

ORD record
ord-12045d6bb6a04fda9c1ba4ec515ac60d
Source dataset
uspto-grants-2008_04
Patent number
US07358268B2

Reaction notes

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