Pyridine → HCID 23371830, compound

HRID 1900056Notes

Reaction equation

HRID 1900056 reaction equation
[CH:1]1([C:8]2[CH:13]=[CH:12][C:11](NC(=O)OCC)=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:20]1C=CC=CC=1.[CH3:26][O:27][CH2:28][CH:29]1[CH2:33][O:32][C:31](=O)[O:30]1>>[CH2:5]1[CH2:4][CH2:3][CH2:2][CH:1]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=2[N:20]2[CH2:33][CH:29]([CH2:28][O:27][CH3:26])[O:30][C:31]2=[O:32])[CH2:7][CH2:6]1

Participants

4

Reactant 3

HCID 1049PyridineHCID 43844854-(Methoxymethyl)-1,3-dioxolan-2-oneHCID 54344752HCID 54344752, compound

Product 1

HCID 23371830HCID 23371830, compoundYield 42.2%

Procedure

4.18 g (16.0 mmol) of ethyl 4-cycloheptylphenylcarbamate were treated with 1.3 g (16.0 mmol) of pyridine and 18 g (0.136 mol) of (RS)-4-methoxymethyl-1,3-dioxolan-2-one and stirred at 160° bath temperature for 20 hours. After cooling the reaction mixture was chromatographed on 400 g of silica gel 60 with ether. After recrystallization from isopropyl ether there were obtained 2.05 g of (RS)-3-[(4-cycloheptyl)phenyl]-5-methoxymethyl-oxazolidin-2-one as a white crystallizate. M.p.: 70°-72°.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. customwas chromatographed on 400 g of silica gel 60 with ether
  3. customAfter recrystallization from isopropyl ether

Sources & evidence

ORD record
ord-35912a6df817408fad1a160e11f57c76
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

Loading…