(3R,9aS)-8-benzyl 2-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)tetrahydro-1H-pyrazino[1,2-a]pyrazine-2,8(9H,9aH)-dicarboxylate → (3R,9aS)-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate

HRID 2175829Notes

Reaction equation

HRID 2175829 reaction equation
[C:1]([C:3]1[C:4]([CH3:37])=[C:5]([C@@H:10]2[CH2:15][N:14]3[CH2:16][CH2:17][N:18](C(OCC4C=CC=CC=4)=O)[CH2:19][C@H:13]3[CH2:12][N:11]2[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2]>CO.[Pd]>[C:1]([C:3]1[C:4]([CH3:37])=[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:30]([O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[O:31])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2]

Participants

4

Reactant 1

HCID 86727054(3R,9aS)-8-benzyl 2-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)tetrahydro-1H-pyrazino[1,2-a]pyrazine-2,8(9H,9aH)-dicarboxylate

Product 1

HCID 86727053(3R,9aS)-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (3R,9aS)-8-benzyl 2-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)tetrahydro-1H-pyrazino[1,2-a]pyrazine-2,8(9H,9aH)-dicarboxylate (600 mg, 1.180 mmol) in MeOH (100 mL) was added Palladium on carbon (10%, 126 mg, 0.118 mmol) and the resulting mixture was subjected to hydrogenation at rt overnight. The reaction mixture was filtered through Celite, washed with mixture of methanol and methylene chloride (1:1) and the filtrate was concentrated to give the title compound: LC/MS: (M+1)+: 375.28.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwashed with mixture of methanol and methylene chloride (1:1)
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-925621c9dc6b41869b3eaded06545fbd
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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