4-Chlorobenzenesulfonyl chloride → 2-(4-Chlorophenylsulfonamido)bicyclo[2.2.1]heptan-7-ol

HRID 1011547Notes

Reaction equation

HRID 1011547 reaction equation
[NH2:1][CH:2]1[CH2:7][CH:6]2[CH:8]([OH:9])[CH:3]1[CH2:4][CH2:5]2.C(N(CC)CC)C.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.C(OCC)(=O)C>O1CCCC1>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:1][CH:2]2[CH2:7][CH:6]3[CH:8]([OH:9])[CH:3]2[CH2:4][CH2:5]3)(=[O:26])=[O:25])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 233660932-Aminobicyclo[2.2.1]heptan-7-ol

Product 1

HCID 594977942-(4-Chlorophenylsulfonamido)bicyclo[2.2.1]heptan-7-olYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-aminobicyclo[2.2.1]heptan-7-ol (prepared according to U.S. Pat. No. 5,583,221) (1.29 g, 10.1 mmol) and triethylamine (1.67 mL, 12 mmol) in 75 mL tetrahydrofuran was added 4-chlorobenzenesulfonyl chloride (2.53 g, 12 mmol). The reaction was stirred at room temperature for 2 h, then diluted into 150 mL ethyl acetate and washed with brine (100 mL). The organic layer was concentrated and purified by flash chromatography on a 40 g silica gel column using a gradient of 10 to 50% ethyl acetate in hexane over 25 min to give 2-(4-chlorophenylsulfonamido)bicyclo[2.2.1]heptan-7-ol (2.12 g, 70%). 1H NMR (400 MHz, CDCl3) δ ppm 7.79-7.81 (1H, m), 7.77-7.79 (1H, m), 7.46-7.48 (1H, m), 7.44-7.46 (1H, m), 5.61 (1H, d, J=10.32 Hz), 4.00 (1H, s), 3.34-3.48 (1H, m), 2.00-2.04 (1H, m), 1.86 (1H, d, J=3.78 Hz), 1.83 (1H, br. s.), 1.68-1.76 (1H, m), 1.59-1.66 (1H, m), 1.37-1.54 (2H, m), 0.97-1.09 (2H, m). LC/MS R.T.=1.98 min; [M+H]+=302.16.

Workup

  1. washwashed with brine (100 mL)
  2. concentrationThe organic layer was concentrated
  3. custompurified by flash chromatography on a 40 g silica gel column
  4. customover 25 min

Sources & evidence

ORD record
ord-988333e0b5a44d49aef6abdd6420e96f
Source dataset
uspto-grants-2011_07
Patent number
US07977362B2

Reaction notes

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