Benzyl 9a-methyl-3-((S)-3-methyl-1-oxoisochroman-6-yl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate → (3S)-3-Methyl-6-(9a-methyloctahydropyrazino[2,1-c][1,4]oxazin-3-yl)isochroman-1-one

HRID 2175787Notes

Reaction equation

HRID 2175787 reaction equation
[CH3:1][C:2]12[CH2:11][N:10](C(OCC3C=CC=CC=3)=O)[CH2:9][CH2:8][N:7]1[CH2:6][CH:5]([C:22]1[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=1)[C:28](=[O:32])[O:27][C@@H:26]([CH3:33])[CH2:25]3)[O:4][CH2:3]2>CO.[Pd]>[CH3:33][C@H:26]1[CH2:25][C:24]2[C:29](=[CH:30][CH:31]=[C:22]([CH:5]3[O:4][CH2:3][C:2]4([CH3:1])[CH2:11][NH:10][CH2:9][CH2:8][N:7]4[CH2:6]3)[CH:23]=2)[C:28](=[O:32])[O:27]1

Participants

4

Reactant 1

HCID 86727034Benzyl 9a-methyl-3-((S)-3-methyl-1-oxoisochroman-6-yl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

Product 1

HCID 71273521(3S)-3-Methyl-6-(9a-methyloctahydropyrazino[2,1-c][1,4]oxazin-3-yl)isochroman-1-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The mixture of Benzyl 9a-methyl-3-((S)-3-methyl-1-oxoisochroman-6-yl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate (215 mg, 0.500 mmol) and 10% Pd-C (56 mg, 0.05 mmol) in MeOH (10 mL) was stirred under a hydrogen balloon for 16 h. After which point, the solution was filtered through Celite and the resulting filtrate was concentrated to afford the title compound: LC/MS: m/e 317.2 (M+H)+.

Workup

  1. filtrationAfter which point, the solution was filtered through Celite
  2. concentrationthe resulting filtrate was concentrated

Sources & evidence

ORD record
ord-ad23376a46144b0ab53327d598632ec2
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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