Pyridine → HCID 58137266, compound

HRID 1752279Notes

Reaction equation

HRID 1752279 reaction equation
[OH:1][CH:2]1[CH:9]2[CH2:10][C:5]3([C:12]([O:14][CH3:15])=[O:13])[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.N1C=CC=CC=1.[Cl:22][C:23](Cl)([O:25]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[Cl:22][C:23]([O:1][CH:2]1[CH:9]2[CH2:10][C:5]3([C:12]([O:14][CH3:15])=[O:13])[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2)=[O:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 3741502Methyl 4-hydroxyadamantane-1-carboxylate

Product 1

HCID 58137266HCID 58137266, compoundYield 272.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of methyl 4-hydroxyadamantane-1-carboxylate (1.01 g, 4.8 mmol) and pyridine (0.38 mL, 4.8 mmol) in CH2Cl2 (25 mL) was cooled in an ice bath and a solution of triphosgene (0.48 g, 1.6 mmol) in CH2Cl2 (10 mL) was added dropwise over 15 min. The ice bath was allowed to melt and the mixture was stirred for 3 h at rt.* The mixture was evaporated to dryness and the residue was triturated with EtOAc (100 mL). The filtrate was concentrated to afford 1-(methoxycarbonyl)-4-adamantyl chloroformate (1.19 g, 91%) as an oil. [* In some experiments the solution of 1-(methoxycarbonyl)-4-adamantyl chloroformate was used directly.]

Workup

  1. custom* The mixture was evaporated to dryness
  2. customthe residue was triturated with EtOAc (100 mL)
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c22fe00ba94d4b58b6e0adb51f7e2652
Source dataset
uspto-grants-2015_10
Patent number
US09163012B2

Reaction notes

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