Pyridine → HCID 58534333, compound

HRID 2174260Notes

Reaction equation

HRID 2174260 reaction equation
[CH3:1][C@H:2]1[CH2:7][C@@H:6]([OH:8])[C@H:5]([CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:3]1.[N:12]1[CH:17]=[CH:16]C=[CH:14][CH:13]=1.Cl[C:19](Cl)([O:21]C(=O)OC(Cl)(Cl)Cl)Cl.C(NCC)C>ClCCl>[CH:9]([C@@H:5]1[CH2:4][CH2:3][C@@H:2]([CH3:1])[CH2:7][C@H:6]1[O:8][C:19](=[O:21])[N:12]([CH2:13][CH3:14])[CH2:17][CH3:16])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 8021DiethylamineHCID 16666(-)-MentholHCID 94429Triphosgene

Product 1

HCID 58534333HCID 58534333, compoundYield 48.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

30 mmol of l-menthol were placed with 110 ml dichlormethane in a 250 ml vessel at room temperature and 3.08 g (39 mmol) of pyridine were added. The reaction mixture was cooled to 0° C. and 3.56 g (12 mmol) of triphosgene in 15 ml dichlormethane were added dropwise. After five minutes 2.37 g (30 mmol) pyridine were added. Subsequently, 2.19 g (30 mmol) of diethylamine in 15 ml dichlormethane were added dropwise, the resulting mixture was allowed to come to ambient temperature and then quenched with water. After separation of the phases, the water phase was extracted once with dichlormethane and the combined organic phases were concentrated. The raw product was purified by distillation and column chromatography to yield 1.5 g of the desired product as a mixture of isomers with a purity of 99.4%.

Workup

  1. customto come to ambient temperature
  2. customquenched with water
  3. customAfter separation of the phases
  4. extractionthe water phase was extracted once with dichlormethane
  5. concentrationthe combined organic phases were concentrated
  6. distillationThe raw product was purified by distillation and column chromatography

Sources & evidence

ORD record
ord-b1a9f9c756394daaa05390ec1f6ce2d2
Source dataset
uspto-grants-2015_06
Patent number
US09060949B2

Reaction notes

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