Pyridine → HCID 86749980, compound

HRID 1900066Notes

Reaction equation

HRID 1900066 reaction equation
C(OC([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)=O)C.[CH3:24][O:25][CH2:26][CH:27]1[CH2:31]O[C:29](=[O:32])[O:28]1.N1C=CC=CC=1>>[CH3:24][O:25][CH2:26][CH:27]1[O:28][C:29](=[O:32])[N:6]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]3[CH2:14][CH2:15][N:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:17][CH2:18]3)=[CH:9][CH:8]=2)[CH2:31]1

Participants

4

Reactant 3

HCID 1049PyridineHCID 43844854-(Methoxymethyl)-1,3-dioxolan-2-oneHCID 23371855HCID 23371855, compound

Product 1

HCID 86749980HCID 86749980, compoundYield 76.9%

Procedure

1.12 g (3.5 mmol) of ethyl 4-(4-ethoxycarbonylamino-phenyl)-piperidine-1-carboxylate were treated with 4.0 g (30.28 mmol) of (RS)-4-(methoxymethyl)-1,3-dioxolan-2-one in the presence of 276.8 mg (3.5 mmol) of pyridine and stirred intensively for 18 hours at an oil bath temperature of 160°. After cooling the reaction mixture was chromatographed on 125 g of silica gel 60 with ether. After recrystallization from methylene chloride/isopropyl ether there were obtained 976 mg of ethyl (RS)-4-[4-(5-methoxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperidine-1-carboxylate. M.p.: 86°-88°.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. customwas chromatographed on 125 g of silica gel 60 with ether
  3. customAfter recrystallization from methylene chloride/isopropyl ether there

Sources & evidence

ORD record
ord-93325644ed4a4a74a78efe39c7ced148
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

Loading…