Sodium Carbonate → (7S,8aS)-7-hydroxymethyl-2-(5-chloropyridin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine

HRID 861369Notes

Reaction equation

HRID 861369 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:11][N:6]2[CH2:7][CH2:8][NH:9][CH2:10][C@@H:5]2[CH2:4]1.Cl[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][N:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CC(C)C>[OH:1][CH2:2][C@@H:3]1[CH2:11][N:6]2[CH2:7][CH2:8][N:9]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][N:14]=3)[CH2:10][C@@H:5]2[CH2:4]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 276852,5-DichloropyridineHCID 45099445HCID 45099445, compound

Product 1

HCID 15886070(7S,8aS)-7-hydroxymethyl-2-(5-chloropyridin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazineYield 29.2%

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

A mixture of 0.50 g (3.2 mmol) of (7S,8aS)-7-hydroxymethyl-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine (Preparation 13, Step A), 2.37 g (16.0 mmol) of 2,5-dichloropyridine, 0.85 g (8.0 mmol) of sodium carbonate and 35 mL of isoamyl alcohol was refluxed for 48 h. The hot solution was filtered and the filtrate evaporated. Purification by flash silica gel chromatography with 9:1 chloroform:methanol gave 0.25 g (29%) of the title compound. 13C NMR (CDCl3): δ 31.1, 37.3, 44.7, 49.7, 51.2, 57.2, 62.5, 66.9, 107.9, 119.9, 137.1, 146.1, 157.6. m/z (MH+) 268.

Workup

  1. temperaturewas refluxed for 48 h
  2. filtrationThe hot solution was filtered
  3. customthe filtrate evaporated
  4. customPurification by flash silica gel chromatography with 9:1 chloroform

Sources & evidence

ORD record
ord-9e62878b51b04898966b78ef6329ca6a
Source dataset
uspto-grants-1998_02
Patent number
US05714487

Reaction notes

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