Hydrochloric Acid → (S)-Octahydropyrazino[2,1-C][1,4]oxazine dihydrochloride

HRID 419390Notes

Reaction equation

HRID 419390 reaction equation
C1(C[N:8]2[CH2:17][CH2:16][N:15]3[C@H:10]([CH2:11][O:12][CH2:13][CH2:14]3)[CH2:9]2)C=CC=CC=1.[ClH:18]>CO.[Pd]>[ClH:18].[ClH:18].[CH2:11]1[C@@H:10]2[CH2:9][NH:8][CH2:17][CH2:16][N:15]2[CH2:14][CH2:13][O:12]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59452873(S)-8-Benzyloctahydropyrazino[2,1-c][1,4]oxazine

Product 1

HCID 66649934(S)-Octahydropyrazino[2,1-C][1,4]oxazine dihydrochlorideYield 52%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To (9aS)-8-(phenylmethyl)octahydropyrazino[2,1-c][1,4]oxazine (1.80 g, 7.70 mmol) in MeOH (30 mL) was added 6N HCl (3.00 mL, 18.0 mmol) followed by Pd on carbon (0.186 g, 10% w/w with starting oxazine). The mixture was placed under H2 (1 atm) overnight. The mixture was filtered through Celite® and washed thoroughly with MeOH to provide the title compound of step G (0.851 g, 4.00 mmol, 52%). 1H NMR (400 MHz, CD3OD) δ ppm 3.26-3.35 (m, 1H), 3.38-3.47 (m, 2H), 3.52-3.57 (m, 1H), 3.65-3.69 (m, 1H), 3.71-3.82 (m, 4H), 3.92-4.00 (m, 1H), 4.02-4.13 (m, 3H).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. washwashed thoroughly with MeOH

Sources & evidence

ORD record
ord-cfe3e2e83eea47348025cd8e9d39a5c6
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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