Sodium Hydroxide → HCID 23371888, compound

HRID 1900053Notes

Reaction equation

HRID 1900053 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[CH:12]=[CH:13][C:14]([N:17]4[CH2:21][CH:20]([CH2:22][O:23][CH3:24])[O:19][C:18]4=[O:25])=[N:15][CH:16]=3)[CH2:7][CH2:6]2)[O:4]CC1.[OH-].[Na+]>O1CCCC1.Cl>[CH3:24][O:23][CH2:22][CH:20]1[O:19][C:18](=[O:25])[N:17]([C:14]2[CH:13]=[CH:12][C:11]([CH:8]3[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]3)=[CH:16][N:15]=2)[CH2:21]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 23371867HCID 23371867, compound

Product 1

HCID 23371888HCID 23371888, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.5 g of (RS)-3-[5-(1,4-dioxa-spiro[4,5]decan-8-yl)-pyridin-2-yl]-5-methoxymethyl-oxazolidin-2-one in 20 ml of tetrahydrofuran and 5 ml of 2N hydrochloric acid was stirred at room temperature for 4 h. Then, 10 ml of 2N sodium hydroxide solution were added and the mixture was extracted several times with ethyl acetate. The organic phases were combined, dried with magnesium sulfate and concentrated. After chromatography with ethyl acetate on silica gel there was obtained 0.4 g of (RS)-5-methoxymethyl-3-[5-(4-oxo-cyclohexyl)-pyridin-2-yl]-oxazolidin-2-one. 1H-nmr (CDCl3) ppm: 8.22 (s, 1H), 8.18 (d,1H), 7.58 (d, 1H), 4.78 (m,1H), 4.27 (t, 1H), 4.09 (t, 1H), 3.64 (m, 2H), 3.43 (s, 3H), 3.08 (m, 1H), 2.51 (m, 4H), 2.04 (bm, 4H).

Workup

  1. extractionthe mixture was extracted several times with ethyl acetate
  2. dry with materialdried with magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-dcebf407d6c14be3a73f2b43dd0e2480
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

Loading…