Isopropyl chloroformate → Isopropyl 4-Hydroxypiperidine-1-carboxylate

HRID 1676207Notes

Reaction equation

HRID 1676207 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.CCN(CC)CC.Cl[C:16]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17]>C(Cl)Cl>[OH:7][CH:4]1[CH2:5][CH2:6][N:1]([C:16]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17])[CH2:2][CH2:3]1

Participants

5

Reactant 3

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

Product 1

HCID 16745126Isopropyl 4-Hydroxypiperidine-1-carboxylateYield 70.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of piperidin-4-ol (5.22 g, 51.6 mmol, Aldrich), Et3N (13.2 mL, 95 mmol, Aldrich) in CH2Cl2 (50 mL) at 0° C. was added a solution of Isopropyl chloroformate (1 Molar in Toluene, 43.0 mL, 43.0 mmol, Aldrich) dropwise. The reaction mixture was stirred at room temperature for 1 h and washed with 1N HCl in H2O. The H2O layer was extracted with DCM (2×). The organic layers were combined and concentrated in vacuo to yield 5.71 g of the desired product as a light brown oil. MS (ESI) 188 (M+H).

Workup

  1. washwashed with 1N HCl in H2O
  2. extractionThe H2O layer was extracted with DCM (2×)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2bcccfe7b8654a359a6d4b88016c7712
Source dataset
uspto-grants-2011_08
Patent number
US08003796B2

Reaction notes

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