(2S,6R)-2-(4-cyclohexyl-phenoxymethyl)-6-ethyl-2,3,5,6-tetrahydro-oxazolo[3,2-a]pyrimidin-7-one → (S)-2-(4-cyclohexyl-phenoxymethyl)-6-ethyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one

HRID 237815Notes

Reaction equation

HRID 237815 reaction equation
[CH:1]1([C:7]2[CH:26]=[CH:25][C:10]([O:11][CH2:12][C@H:13]3[O:24][C:16]4=[N:17][C:18](=[O:23])[C@H:19]([CH2:21][CH3:22])[CH2:20][N:15]4[CH2:14]3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C1(C)C=CC=CC=1.[O-2].[Mn+4].[O-2]>[CH:1]1([C:7]2[CH:26]=[CH:25][C:10]([O:11][CH2:12][C@H:13]3[O:24][C:16]4=[N:17][C:18](=[O:23])[C:19]([CH2:21][CH3:22])=[CH:20][N:15]4[CH2:14]3)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 25074227(2S,6R)-2-(4-cyclohexyl-phenoxymethyl)-6-ethyl-2,3,5,6-tetrahydro-oxazolo[3,2-a]pyrimidin-7-one

Product 1

HCID 25071737(S)-2-(4-cyclohexyl-phenoxymethyl)-6-ethyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-oneYield 5.5%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of (2S,6R)-2-(4-cyclohexyl-phenoxymethyl)-6-ethyl-2,3,5,6-tetrahydro-oxazolo[3,2-a]pyrimidin-7-one (108 mg, 0.41 mmol) in toluene (2 ml) was added manganese(IV) oxide (360 mg, 4.1 mmol). The reaction mixture was heated at reflux for three days. The reaction mixture was filtered without cooling and the filtrate concentrated and loaded on a silica gel column. The column was eluted with 2-7% isopropanol/methylene chloride to afford 8 mg of (S)-2-(4-cyclohexyl-phenoxymethyl)-6-ethyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one. [α]D25 −22.40 (c 0.5, CHCl3).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for three days
  3. filtrationThe reaction mixture was filtered
  4. temperaturewithout cooling
  5. concentrationthe filtrate concentrated
  6. washThe column was eluted with 2-7% isopropanol/methylene chloride

Sources & evidence

ORD record
ord-9f005d1294354a449e89b826dd07d5c6
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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