(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 1502004Notes

Reaction equation

HRID 1502004 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-af55198487164936b72db0abae6fa2af
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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