4-Piperidinecarboxylic acid → HCID 61800653, compound

HRID 423682Notes

Reaction equation

HRID 423682 reaction equation
Cl[C:2]([O:4][CH:5]([CH3:7])[CH3:6])=[O:3].[NH:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1.[OH-].[Na+]>O>[CH3:6][CH:5]([O:4][C:2]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)=[O:3])[CH3:7]

Participants

5

Reactant 3

HCID 37734-Piperidinecarboxylic acidHCID 7917Isopropyl chloroformateHCID 14798Sodium Hydroxide

Product 1

HCID 61800653HCID 61800653, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Isopropyl chloroformate (1.0M in toluene, 55 mL, 55 mmol) was added dropwise to a mixture of 4-piperidinecarboxylic acid (6.5 g, 50 mmol) and sodium hydroxide (4.4 g, 110 mmol) in water (25 mL) at ambient temperature. The mixture was stirred at ambient temperature overnight. The aqueous phase was separated and adjusted to pH=1 with concentrated HCl. The aqueous phase was extracted with EtOAc, and the organics were dried over MgSO4, filtered, and the filtrate was concentrated to give 10.2 g (95%) of 1-{[(1-methylethyl)oxy]carbonyl}-4-piperidinecarboxylic acid as a white solid. 1H NMR (400 MHz, CDCl3): δ 4.89 (septet, 1H, J=6.2 Hz), 4.04 (d, 2H, J=3.9 Hz), 2.97-2.79 (m, 2H), 2.58-2.38 (m, 1H), 2.00-1.80 (m, 2H), 1.72-1.53 (m, 2H), 1.21 (d, 6H, J=6.3 Hz); LRMS (ESI), m/z 214 (M−H).

Workup

  1. customThe aqueous phase was separated
  2. extractionThe aqueous phase was extracted with EtOAc
  3. dry with materialthe organics were dried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-aed6f1a454c542e4abbc2e604bfb8dac
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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