Sodium Hydroxide → tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2h)-pyridinecarboxylate

HRID 861448Notes

Reaction equation

HRID 861448 reaction equation
C(O[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])(C)(C)C.[NH:13]1[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20][CH2:21][OH:22])[CH2:15][CH2:14]1.[OH-].[Na+]>O1CCOCC1>[C:8]([O:7][C:6]([N:13]1[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20][CH2:21][OH:22])[CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 814974-PiperidinepropanolHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 2800739tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2h)-pyridinecarboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 6 g of di(tert-butyl)carbonate in 20 ml of dioxan was introduced into a solution of 3.2 g of 3-(4-piperidinyl)propanol in 50 ml of dioxan containing 25 ml of a 2N aqueous solution of sodium hydroxide, cooled at 0° C. The mixture was allowed to react for 16 hours at room temperature. The solution was then evaporated and the residue was extracted with ethylether. The organic layer was washed with a 10% solution of KHSO4 and then dried over MgSO4.

Workup

  1. customto react for 16 hours at room temperature
  2. customThe solution was then evaporated
  3. extractionthe residue was extracted with ethylether
  4. washThe organic layer was washed with a 10% solution of KHSO4
  5. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-e656f59a5b75464dafdfadc5d8ced98a
Source dataset
uspto-grants-1998_02
Patent number
US05714497

Reaction notes

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