Isopropyl chloroformate → 4-Tert-butoxycarbonylamino-piperidine-1-carboxylic acid isopropyl ester

HRID 448583Notes

Reaction equation

HRID 448583 reaction equation
[C:1]([NH:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.Cl[C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24]>C(Cl)Cl>[CH:26]([O:25][C:23]([N:12]1[CH2:13][CH2:14][CH:9]([NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:10][CH2:11]1)=[O:24])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 597771674-Tert-butoxycarbonylamino-piperidine-1-carboxylic acid isopropyl esterYield 87.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(N-Boc amino)piperidine (2.61 g, 13 mmol) and triethylamine (3 mL, 21.5 mmol) in 25 mL of DCM, was added isopropyl chloroformate (1 M in toluene, 13.1 mL, 13.1 mmol). The mixture was stirred at room temperature for 20 h. It was then washed with a saturated solution of NaHCO3 (50 mL), followed by brine (50 mL). The solution was dried, filtered and evaporated to afford 3.26 g (87%) of 18a.

Workup

  1. washIt was then washed with a saturated solution of NaHCO3 (50 mL)
  2. customThe solution was dried
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-df6246defcba4e8f9517be0d1071a7fb
Source dataset
uspto-grants-2013_07
Patent number
US08481731B2

Reaction notes

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