Tert-butyl 4-iodopiperidine-1-carboxylate → HCID 53748621, compound

HRID 2298084Notes

Reaction equation

HRID 2298084 reaction equation
I[CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](=[S:24])([O-:23])=[O:22])=[CH:17][CH:16]=1.[K+]>C(O)C>[C:11]([O:10][C:8]([N:5]1[CH2:6][CH2:7][CH:2]([S:24][S:21]([C:18]2[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=2)(=[O:23])=[O:22])[CH2:3][CH2:4]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 10892302Tert-butyl 4-iodopiperidine-1-carboxylateHCID 23662126Benzenesulfonothioic acid, 4-methyl-, potassium salt

Product 1

HCID 53748621HCID 53748621, compoundYield 41.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Iodo-piperidine-1-carboxylic acid, tert-butyl ester (1.3 g) and potassium toluene-4-thiosulfonate (1.0 g) were combined in ethanol (10 ml) with cis-dicyclohexane 18-crown-6 (10 mg) and heated under reflux for 12 h. After cooling the reaction mixture was partitioned between ethyl acetate and water, the organic layer was separated, washed with water and brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluting with iso-hexane/ethyl acetate 4:1 to 7:3), to yield the subtitle compound as an oil (0.65 g).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 12 h
  3. temperatureAfter cooling the reaction mixture
  4. customwas partitioned between ethyl acetate and water
  5. customthe organic layer was separated
  6. washwashed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel chromatography (eluting with iso-hexane/ethyl acetate 4:1 to 7:3)

Sources & evidence

ORD record
ord-21bced64890145c488b6e1c9cf0cab0a
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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