HCID 22940607, compound → (Octahydro-2H-pyrido[1,2-a]pyrazin-7-yl)methanol

HRID 1977054Notes

Reaction equation

HRID 1977054 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]2[CH2:14][C@@H:15]([CH2:18][OH:19])[CH2:16][CH2:17][C@H:10]2[CH2:9]1)(OC(C)(C)C)=O>FC(F)(F)C(O)=O.O>[OH:19][CH2:18][C@@H:15]1[CH2:14][N:11]2[CH2:12][CH2:13][NH:8][CH2:9][C@@H:10]2[CH2:17][CH2:16]1

Participants

4

Reactant 1

HCID 22940607HCID 22940607, compound

Product 1

HCID 9855588(Octahydro-2H-pyrido[1,2-a]pyrazin-7-yl)methanolYield 92.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 5.84 g (21.6 mmol) of (7S,9aS)-N-BOC-7-hydroxymethyl-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine (WO 93/25552) in 140 mL of trifluoroacetic acid and 60 mL of water was stirred at room temperature for 16 h. The mixture was concentrated and the residue dissolved in water. The aqueous phase saturated with solid sodium carbonate and extracted with chloroform (3×). The combined organic layers were dried (magnesium sulfate), filtered and evaporated to give 3.39 g (92%) of the title compound. This material was used without further purification for subsequent reactions. 13C NMR (base, d-6 DMSO): δ24.8, 25.1, 36.0, 45.7, 51.9, 56.1, 56.7, 62.0, 62.7.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue dissolved in water
  3. extractionThe aqueous phase saturated with solid sodium carbonate and extracted with chloroform (3×)
  4. dry with materialThe combined organic layers were dried (magnesium sulfate)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-fb6080d3c5fe4726bf798096dd3fb4b5
Source dataset
uspto-grants-2001_05
Patent number
US06231833B1

Reaction notes

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