Pyridine → 2-adamantyl Chloroformate

HRID 326721Notes

Reaction equation

HRID 326721 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[OH:11])[CH2:8]2.[Cl:12][C:13](Cl)([O:15]C(=O)OC(Cl)(Cl)Cl)Cl.N1C=CC=CC=1>C(Cl)Cl>[Cl:12][C:13]([O:11][CH:2]1[CH:3]2[CH2:9][CH:7]3[CH2:6][CH:5]([CH2:10][CH:1]1[CH2:8]3)[CH2:4]2)=[O:15]

Participants

5

Reactant 3

HCID 1049PyridineHCID 641492-AdamantanolHCID 94429Triphosgene

Product 1

HCID 108785372-adamantyl ChloroformateYield 207.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-adamantanol (912 mg, 5.99 mmol) in methylene chloride (15 mL), at 0° C. under nitrogen, was added a solution of triphosgene (653 mg, 2.2 mmol) and pyridine (484 μL, 5.99 mmol) in methylene chloride. The reaction mixture was stirred at ambient temperature for 3 hours and then concentrated to dryness under reduced pressure. Ethyl acetate was added to the residue and the resultant mixture was filtered. The filtrate was concentrated in vacuo to give 980 mg of the title compound as a white powder. 1H NMR (CDCl3) δ1.5-2.2 (m, 14H), 5.02 (m, 1H).

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. additionEthyl acetate was added to the residue
  3. filtrationthe resultant mixture was filtered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7542839594044763989280a129f3bb2e
Source dataset
uspto-grants-1993_12
Patent number
US05270302

Reaction notes

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