Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 59611709, compound

HRID 1022289Notes

Reaction equation

HRID 1022289 reaction equation
[OH:1][C@H:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:3][C:4]([O:6][CH3:7])=[O:5].ClC(Cl)(Cl)C(=N)O[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C(Cl)Cl>[CH3:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][O:1][C@H:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:3][C:4]([O:6][CH3:7])=[O:5])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 98349453R-hydroxymyristic acid methyl esterHCID 110872634-Methoxybenzyl 2,2,2-Trichloroacetimidate

Product 1

HCID 59611709HCID 59611709, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 30 (3.50 g, 12.9 mmol) and 4-methoxybenzyl trichloroacetimidate (4.65 g, 17.3 mmol) in DCM (100 mL) was added camphorsulfonic acid (450 mg, 1.92 mmol). The mixture was stirred overnight at room temperature. The mixture was washed with a saturated solution of NaHCO3 (300 mL) and water (300 mL) and dried over Na2SO4. The drying agent was removed by filtration and the solvents removed using a rotary evaporator. The residue was purified by chromatography on silica gel (120 g RediSep column, eluting with a gradient of 0% through 30% ethyl acetate/hexanes over 70 min, 85 mL/min) to give the product 32 (4.01 g, 81%) as a colorless liquid.

Workup

  1. washThe mixture was washed with a saturated solution of NaHCO3 (300 mL) and water (300 mL)
  2. dry with materialdried over Na2SO4
  3. customThe drying agent was removed by filtration
  4. customthe solvents removed
  5. customa rotary evaporator
  6. customThe residue was purified by chromatography on silica gel (120 g RediSep column
  7. washeluting with a gradient of 0% through 30% ethyl acetate/hexanes over 70 min

Sources & evidence

ORD record
ord-b1f664fa6258452b8d3905e75d325426
Source dataset
uspto-grants-2014_05
Patent number
US08722064B2

Reaction notes

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