Isopropyl 4-Hydroxypiperidine-1-carboxylate → HCID 86597364, compound

HRID 2377918Notes

Reaction equation

HRID 2377918 reaction equation
Cl[C:2]1[C:7]([CH2:8][CH3:9])=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=1.[CH:11]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]1)=[O:16])([CH3:13])[CH3:12].CC(C)([O-])C.[K+]>C1COCC1>[CH:11]([O:14][C:15]([N:17]1[CH2:18][CH2:19][CH:20]([O:23][C:2]2[C:7]([CH2:8][CH3:9])=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=2)[CH2:21][CH2:22]1)=[O:16])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 16745126Isopropyl 4-Hydroxypiperidine-1-carboxylateHCID 21828432HCID 21828432, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 86597364HCID 86597364, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4,6-dichloro-5-ethyl-pyrimidine (1 g, 5.65 mmol) and 4-hydroxy-piperidine-1-carboxylic acid isopropyl ester (1.05 g, 5.65 mmol) in dry THF under nitrogen at 0° C., potassium tert-butoxide (1M solution in THF, 6.78 mL) was added dropwise. The reaction was stirred at rt for 30 min. The mixture was quenched with water and extracted with EtOAc (3×). The organic layer was washed with water, sat. NH4Cl and brine, followed by drying over sodium sulfate and concentration under vacuo. The resulting oil was purified by HPLC to afford 4-(6-chloro-5-ethyl-pyrimidin-4-yloxy)-piperidine-1-carboxylic acid isopropyl ester (0.74 g, 39.8%) as a colorless oil. Exact mass calculated for C15H22ClN3O3 327.13, found 328.2 (MH+).

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc (3×)
  3. washThe organic layer was washed with water, sat. NH4Cl and brine
  4. dry with materialby drying over sodium sulfate and concentration under vacuo
  5. customThe resulting oil was purified by HPLC

Sources & evidence

ORD record
ord-4fb8265574374a648829b2668808b923
Source dataset
uspto-grants-2008_12
Patent number
US07470699B2

Reaction notes

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