(3S,9aS)-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate → (3R,9aR)-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate
Reaction equation
[C:1]([C:3]1[C:4]([CH3:27])=[C:5]([C@H:10]2[CH2:15][N:14]3[CH2:16][CH2:17][NH:18][CH2:19][C@H:13]3[CH2:12][N:11]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].C(N1[C@H](C2C=CC(F)=C(C#N)C=2C)CN2CCN(C(OCC3C=CC=CC=3)=O)C[C@@H]2C1)C=C>>[C:1]([C:3]1[C:4]([CH3:27])=[C:5]([C@@H:10]2[CH2:15][N:14]3[CH2:16][CH2:17][NH:18][CH2:19][C@@H:13]3[CH2:12][N:11]2[C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].[C:1]([C:3]1[C:4]([CH3:27])=[C:5]([C@H:10]2[CH2:15][N:14]3[CH2:16][CH2:17][NH:18][CH2:19][C@@H:13]3[CH2:12][N:11]2[C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2]Participants
4
Reactant 2
Product 2
Procedure
The title compound was prepared in an analogous fashion to that described for the synthesis of (3S,9aS)-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate starting from (7R,9aS)-benzyl 8-allyl-7-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate (obtained from the synthesis of (3S,9aR)-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate). LC/MS: 375.14 (M+1)+.
Sources & evidence
- ORD record
- ord-077594b9de224da38216be72222d7998
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09062070B2
Reaction notes
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