4-(Methoxymethyl)-1,3-dioxolan-2-one → t-butyl (RS)-4-[4-(5-methoxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperidine-1-carboxylate

HRID 1900063Notes

Reaction equation

HRID 1900063 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][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)=O)C.[CH3:26][O:27][CH2:28][CH:29]1[CH2:33]O[C:31](=[O:34])[O:30]1>N1C=CC=CC=1>[CH3:26][O:27][CH2:28][CH:29]1[O:30][C:31](=[O:34])[N:6]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]3[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]3)=[CH:9][CH:8]=2)[CH2:33]1

Participants

4

Reactant 2

HCID 43844854-(Methoxymethyl)-1,3-dioxolan-2-oneHCID 23371871t-Butyl 4-(4-ethoxycarbonylamino-phenyl)-piperidine-1-carboxylate

Product 1

HCID 86749979t-butyl (RS)-4-[4-(5-methoxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperidine-1-carboxylateYield 58%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5.5 g (15.0 mmol) of t-butyl 4-(4-ethoxycarbonylamino-phenyl)-piperidine-1-carboxylate and 20 g (0.15 mol) of (RS)-4-(methoxymethyl)-1,3-dioxolan-2-one were stirred intensively in the presence of 2.37 g of pyridine for 18 hours at an oil bath temperature of 160°. After cooling the reaction mixture it was chromatographed on 840 g of silica gel 60 with ether. 3.4 g of t-butyl (RS)-4-[4-(5-methoxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperidine-1-carboxylate were obtained as a yellowish oil. 1H-NMR (CDCl3) ppm: 7.48 (d,2H), 7.22 (d,2H), 4.76 (m,1H), 4.25 (bd,2H), 4.05 (t,1H), 3.92 (t,1H), 3.64 (d,2H), 3.43 (s,3H), 2.80 (t,2H), 2.64 (m,1H), 1.78 (bd,2H), 1.61 (m,2H), 1.49 (s,9H).

Workup

  1. temperatureAfter cooling the reaction mixture it
  2. customwas chromatographed on 840 g of silica gel 60 with ether

Sources & evidence

ORD record
ord-a6479b7751ff406e8cfc11632c7cbe18
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

Loading…