(3S)-3-Methyl-6-(9a-methyloctahydropyrazino[2,1-c][1,4]oxazin-3-yl)isochroman-1-one → (3R)-3-Methyl-6-(9a-methyloctahydropyrazino[2,1-c][1,4]oxazin-3-yl)isochroman-1-one

HRID 1501964Notes

Reaction equation

HRID 1501964 reaction equation
[CH3:1][C@H:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:12]3[O:17][CH2:16][C:15]4([CH3:22])[CH2:18][NH:19][CH2:20][CH2:21][N:14]4[CH2:13]3)[CH:9]=2)[C:4](=[O:23])[O:3]1.C[C@@H]1CC2C(=CC=C(C3CO3)C=2)C(=O)O1>>[CH3:1][C@@H:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:12]3[O:17][CH2:16][C:15]4([CH3:22])[CH2:18][NH:19][CH2:20][CH2:21][N:14]4[CH2:13]3)[CH:9]=2)[C:4](=[O:23])[O:3]1

Participants

3

Reactant 2

HCID 71273521(3S)-3-Methyl-6-(9a-methyloctahydropyrazino[2,1-c][1,4]oxazin-3-yl)isochroman-1-oneHCID 86693039(3R)-3-methyl-6-(oxiran-2-yl)-3,4-dihydro-1H-isochromen-1-one

Product 1

HCID 89633313(3R)-3-Methyl-6-(9a-methyloctahydropyrazino[2,1-c][1,4]oxazin-3-yl)isochroman-1-one

Procedure

The title compound was prepared in an analogous fashion to that described for (3S)-3-Methyl-6-(9a-methyloctahydropyrazino[2,1-c][1,4]oxazin-3-yl)isochroman-1-one starting from (3R)-3-methyl-6-(oxiran-2-yl) isochroman-1-one. LC/MS: m/e 317.2 (M+H)+.

Sources & evidence

ORD record
ord-65153c0cd676498dba1eb64cd4b696d6
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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