Sulfuric Acid → HCID 58695824, compound

HRID 1178891Notes

Reaction equation

HRID 1178891 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:14][CH:13]3[N:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:10]([CH2:11][CH2:12]3)[CH2:9]2)=[C:4]([CH:21](O)[CH2:22][CH3:23])[CH:3]=1.[OH:25]S(O)(=O)=O.[C:30](#[N:32])[CH3:31]>>[C:30]([NH:32][CH:21]([C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[CH:8]1[CH2:14][CH:13]2[N:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:10]([CH2:11][CH2:12]2)[CH2:9]1)[CH2:22][CH3:23])(=[O:25])[CH3:31]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 6342Acetonitrile2×HCID 58695801HCID 58695801, compound

Product 1

HCID 58695824HCID 58695824, compound

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 3-[4-chloro-2-(1-hydroxypropyl)phenyl]-8-azabicyclo[3.2.1]octane-8-carboxylate (2-8) (2.25 g, 6.39 mmol) in acetonitrile (100 mL) was add concentrated H2SO4 (5.11 mL, 95.9 mmol) in 50 mL of acetonitrile. The mixture was stirred at 60° C. for 1 h, quenched with 1 N NaOH (200 mL), and extracted with EtOAc (3×200 mL). The combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. Purification of the crude residue by flash chromatography over silica gel (a mixture of 9:1:0.1 methylenechloride:MeOH:30% NH4OH as eluent) afforded (2-9) as a white solid.

Workup

  1. customquenched with 1 N NaOH (200 mL)
  2. extractionextracted with EtOAc (3×200 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the crude residue by flash chromatography over silica gel (
  8. additiona mixture of 9:1:0.1 methylenechloride

Sources & evidence

ORD record
ord-e670896df6d6491fa66a65e527cd5b37
Source dataset
uspto-grants-2007_10
Patent number
US07276520B2

Reaction notes

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