tert-Butyl (3R)-3-(hydroxymethyl)piperazine-1-carboxylate → (3S,9aR)-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate

HRID 2175830Notes

Reaction equation

HRID 2175830 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].FC1C(C#N)=C(C)C(C2CO2)=CC=1.OC[C@@H]1NCCN(C(OC(C)(C)C)=O)C1>>[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 3

HCID 24820286tert-Butyl (3R)-3-(hydroxymethyl)piperazine-1-carboxylateHCID 866473076-Fluoro-2-methyl-3-(oxiran-2-yl)benzonitrileHCID 86727053(3R,9aS)-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate

Product 1

HCID 86727055(3S,9aR)-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-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-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate starting from 6-fluoro-2-methyl-3-(oxiran-2-yl)benzonitrile and (R)-tert-butyl 3-(hydroxymethyl)piperazine-1-carboxylate. LC/MS: 375.16 (M+1)+.

Sources & evidence

ORD record
ord-814d3254b2714c6f92286eee4bd6d044
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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