6-fluoro-2-methyl-3-((3S,9aR)-octahydropyrazino[2,1-c][1,4]oxazin-3-yl)benzonitrile → (3S,9aR)-tert-butyl 3-(3-cyano-4-fluoro-2,5-dimethylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

HRID 1502079Notes

Reaction equation

HRID 1502079 reaction equation
[C:1]([C:3]1[C:4]([CH3:28])=[C:5]([C@H:11]2[O:16][CH2:15][C@@H:14]3[CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:20][N:13]3[CH2:12]2)[CH:6]=[C:7]([CH3:10])[C:8]=1[F:9])#[N:2].FC1C(C#N)=C(C)C([C@@H]2OC[C@H]3CNCCN3C2)=CC=1>>[C:1]([C:3]1[C:4]([CH3:28])=[C:5]([C@@H:11]2[O:16][CH2:15][C@H:14]3[CH2:17][N:18]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[CH2:19][CH2:20][N:13]3[CH2:12]2)[CH:6]=[C:7]([CH3:10])[C:8]=1[F:9])#[N:2]

Participants

3

Reactant 2

HCID 712736236-fluoro-2-methyl-3-((3S,9aR)-octahydropyrazino[2,1-c][1,4]oxazin-3-yl)benzonitrileHCID 89633504(3R,9aS)-tert-butyl 3-(3-cyano-4-fluoro-2,5-dimethylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

Product 1

HCID 89633503(3S,9aR)-tert-butyl 3-(3-cyano-4-fluoro-2,5-dimethylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

Procedure

The title compound was prepared in an analogous fashion to that described for the synthesis of (3R,9aS)-tert-butyl 3-(3-cyano-4-fluoro-2,5-dimethylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate starting from 6-fluoro-2-methyl-3-((3S,9aR)-octahydropyrazino[2,1-c][1,4]oxazin-3-yl)benzonitrile.

Sources & evidence

ORD record
ord-8fe9ba3857ba418b8e924c3786849b65
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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