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

HRID 237808Notes

Reaction equation

[CH:1]1([C:7]2[CH:25]=[CH:24][C:10]([O:11][CH2:12][C@H:13]3[O:23][C:16]4=[N:17][C:18](=[O:22])[C@@H:19]([CH3:21])[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:25]=[CH:24][C:10]([O:11][CH2:12][C@H:13]3[O:23][C:16]4=[N:17][C:18](=[O:22])[C:19]([CH3:21])=[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

Conditions

Temperature: 110 °C

Procedure

To a solution of (2S,6S)-2-(4-cyclohexyl-phenoxymethyl)-6-methyl-2,3,5,6-tetrahydro-oxazolo[3,2-a]pyrimidin-7-one (38 mg, 0.111 mmol) in toluene (3 ml) was added 96 mg (1.11 mmol) of manganese(IV) oxide. The reaction mixture was heated at 110° C. overnight. The reaction mixture was filtered and the filtrate concentrated and loaded onto a silica gel column, and eluted with 2-7% isopropanol/methylene chloride to afford 8 mg of (S)-2-(4-cyclohexyl-phenoxymethyl)-6-methyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one.

Workup

filtrationThe reaction mixture was filtered
concentrationthe filtrate concentrated
washeluted with 2-7% isopropanol/methylene chloride

Sources & evidence

ORD record: ord-133676b0477244e5a1d294ba807a7c95
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642603B2

Reaction notes

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