Tert-Butylamine → HCID 58695796, compound

HRID 1178885Notes

Reaction equation

HRID 1178885 reaction equation
[CH:1]1([C:7]2([C:20]([OH:22])=O)[CH2:13][CH:12]3[N:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:9]([CH2:10][CH2:11]3)[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.[C:29]([NH2:33])([CH3:32])([CH3:31])[CH3:30]>C(Cl)(Cl)Cl.CN(C=O)C>[C:29]([NH:33][C:20]([C:7]1([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:13][CH:12]2[N:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:9]([CH2:10][CH2:11]2)[CH2:8]1)=[O:22])([CH3:32])([CH3:31])[CH3:30]

Participants

6

Reactant 3

HCID 6385Tert-ButylamineHCID 65578Oxalyl chlorideHCID 58695786HCID 58695786, compound

Product 1

HCID 58695796HCID 58695796, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-cyclohexyl-8-(ethoxycarbonyl)-8-azabicyclo[3.2.1]octane-3-carboxylic acid (1-7) (1.50 g, 4.85 mmol) in CHCl3 (60.0 mL) was slowly added oxalyl chloride (2.67 mL, 5.33 mmol, 2.0 N), followed by addition of DMF (3 drops) as a catalyst. After the bubbling ceased, the mixture was stirred for 30 min and the solvents were removed under vacuum. To the mixture was added t-BuNH2 (5.32 g, 72.7 mmol) and the resulting suspension was warmed up to 80° C. overnight. The solvents were removed under vacuum; the reaction was quenched with 1 N HCl, and then extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated to give a crude residue. Purification of the crude residue by flash chromatography over silica gel (10% ethyl acetate/hexanes as eluent) afforded (1-8) as a white solid.

Workup

  1. customthe solvents were removed under vacuum
  2. customThe solvents were removed under vacuum
  3. customthe reaction was quenched with 1 N HCl
  4. extractionextracted with EtOAc (3×100 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated
  8. customto give a crude residue
  9. customPurification of the crude residue by flash chromatography over silica gel (10% ethyl acetate/hexanes as eluent)

Sources & evidence

ORD record
ord-01f0fd65988444f5ab64d6277296eb65
Source dataset
uspto-grants-2007_10
Patent number
US07276520B2

Reaction notes

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