Diisopropylamine → Tert-butyl 3-cyclohexyl-3-{[(methylsulfonyl)oxy]methyl}-8-azabicyclo[3.2.1]octane-8-carboxylate

HRID 1178896Notes

Reaction equation

HRID 1178896 reaction equation
[CH:1]1([C:7]2([CH2:22][OH:23])[CH2:13][CH:12]3[N:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[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(NC(C)C)(C)C.CN(C1C=CC=CN=1)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>C(Cl)Cl>[CH:1]1([C:7]2([CH2:22][O:23][S:41]([CH3:40])(=[O:43])=[O:42])[CH2:13][CH:12]3[N:14]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH:9]([CH2:10][CH2:11]3)[CH2:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 218852-DimethylaminopyridineHCID 31297Methanesulfonyl chlorideHCID 58695788Tert-butyl 3-cyclohexyl-3-(hydroxymethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate

Product 1

HCID 86607399Tert-butyl 3-cyclohexyl-3-{[(methylsulfonyl)oxy]methyl}-8-azabicyclo[3.2.1]octane-8-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 3-cyclohexyl-3-(hydroxymethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate (3-3) (0.870 g, 2.69 mmol) in methylene chloride was added diisopropylamine (0.562 mL, 3.23 mmol), dimethylaminopyridine (32.5 mg, 0.269 mmol), and methanesulfonyl chloride (0.229 mL, 2.97 mmol). The mixture was stirred at room temperature for four hours and diluted with methylene chloride, washed with water, a saturated aqueous solution of NaHCO3, and 1 N HCl aqueous solution, dried over anhydrous MgSO4, filtered, and concentrated to give (3-4) as a colorless oil.

Workup

  1. washwashed with water
  2. dry with materiala saturated aqueous solution of NaHCO3, and 1 N HCl aqueous solution, dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ba7c979c17a2464e959e2979908366ec
Source dataset
uspto-grants-2007_10
Patent number
US07276520B2

Reaction notes

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