Isopropyl chloroformate → Isopropyl 4-Hydroxypiperidine-1-carboxylate

HRID 448555Notes

Reaction equation

HRID 448555 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)CC)C.Cl[C:16]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17]>C(Cl)Cl.C1(C)C=CC=CC=1>[CH:19]([O:18][C:16]([N:5]1[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]1)=[O:17])([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 79341Piperidin-4-ol

Product 1

HCID 16745126Isopropyl 4-Hydroxypiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydroxyl-piperidine (8.1 g, 80 mmol) and triethylamine (11.2 mL, 1 eq) in 200 mL of DCM, was added isopropyl chloroformate (80 mL of a 1 M solution in toluene, 1 eq). The reaction mixture was stirred at room temperature for 3 h, quenched with a saturated solution of bicarbonate and extracted with DCM twice. The combined extracts were washed with a saturated solution of bicarbonate, dried over magnesium sulfate and evaporated to give 2a.

Workup

  1. customquenched with a saturated solution of bicarbonate
  2. extractionextracted with DCM twice
  3. washThe combined extracts were washed with a saturated solution of bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-fcd2ae03387a42e39633dd70719442d2
Source dataset
uspto-grants-2013_07
Patent number
US08481731B2

Reaction notes

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