Sodium Sulfate → HCID 86621359, compound

HRID 1878661Notes

Reaction equation

HRID 1878661 reaction equation
[N:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([C:4]3=O)[CH2:2]1)[CH2:8]2.[NH2:12][C:13]1[CH:14]=[N:15][C:16]([Cl:19])=[CH:17][CH:18]=1.[O-]S([O-])(=O)=O.[Na+].[Na+].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CC(O)=O>[Cl:19][C:16]1[N:15]=[CH:14][C:13]([NH:12][C@H:4]2[CH:5]3[CH2:10][N:1]4[CH2:8][CH:7]([CH2:9][CH:3]2[CH2:2]4)[CH2:6]3)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 24436Sodium SulfateHCID 793055-Amino-2-chloropyridineHCID 1426421-Azatricyclo(3.3.1.1,3,7)decan-4-oneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 86621359HCID 86621359, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1-azatricyclo[3.3.1.13,7]decan-4-one (1.51 g, 10 mmol; see Becker, D. P.; Flynn, D. L. Synthesis 1992, 1080) in HOAc (50 mL) was treated with 3-amino-6-chloropyridine (1.90 g, 15 mmol; Aldrich), anhydrous Na2SO4 (18.5 g, 0.13 mol; Aldrich), and NaBH(OAc)3 (4.22 g, 20 mmol; Aldrich) and was stirred at ambient temperature for 10 hours. After the reaction was complete, the solid was filtered off, and the filtrate was concentrated. The residue was carefully basified with saturated aqueous Na2CO3 (pH 10), extracted with CHCl3 (3×100 mL), and the combined extracts were purified by flash chromatography [silica gel, ammonium hydroxide-methanol-chloroform (2:10:90)] to afford the title compounds:

Workup

  1. filtrationthe solid was filtered off
  2. concentrationthe filtrate was concentrated
  3. extractionextracted with CHCl3 (3×100 mL)
  4. customthe combined extracts were purified by flash chromatography [silica gel, ammonium hydroxide-methanol-chloroform (2:10:90)]

Sources & evidence

ORD record
ord-428ccc5ee3c84b4f888a9d830028f53b
Source dataset
uspto-grants-2012_11
Patent number
US08314119B2

Reaction notes

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