Pyridine → 5-(Methoxymethyl)oxazolidin-2-one

HRID 1900057Notes

Reaction equation

HRID 1900057 reaction equation
C12(C3C=C[C:14]([NH:17][C:18](=[O:22])[O:19][CH2:20][CH3:21])=CC=3)CC3CC(CC(C3)C1)C2.N1C=CC=CC=1.[CH3:29][O:30]CC1COC(=O)O1>>[CH3:29][O:30][CH2:21][CH:20]1[O:19][C:18](=[O:22])[NH:17][CH2:14]1

Participants

4

Reactant 3

HCID 1049PyridineHCID 43844854-(Methoxymethyl)-1,3-dioxolan-2-oneHCID 23371868Ethyl 4-adamantan-1-yl-phenyl-carbamate

Product 1

HCID 103131495-(Methoxymethyl)oxazolidin-2-one

Procedure

5.42 g (18.1 mmol) of ethyl 4-adamantan-1-yl-phenylcarbamate were treated with 1.43 g (18.1 mmol) of pyridine and 18.0 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 500 g of silica gel 60 with ether. 1.4 g of (RS)-3-(4-adamantan-1-yl)phenyl]-5-methoxymethyl-oxazolidin-2-one were obtained as a white crystallizate after recrystallization from methylene chloride/ether. M.p.: 145°-147°.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. customwas chromatographed on 500 g of silica gel 60 with ether

Sources & evidence

ORD record
ord-ae3c4df9a0684cc7bc8072230a38625e
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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