Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 18391989, compound

HRID 1872755Notes

Reaction equation

HRID 1872755 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([OH:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[C:15]1(C)[C:19]2(CS(O)(=O)=O)[C:20](C[CH:16]1[CH2:17]C2)=[O:21]>O1C=CCCC1>[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][CH:20]2[CH2:19][CH2:15][CH2:16][CH2:17][O:21]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 643472(R)-(+)-1-Benzyl-3-pyrrolidinol

Product 1

HCID 18391989HCID 18391989, compoundYield 120%

Reagents, catalysts & solvents 1

HCID 80803,4-dihydro-2H-pyranSolvent

Procedure

To a stirred solution of (R)-(+)-1-benzyl-3-pyrrolidinol (5.00 g, 28 mmol) and D-camphor-10-sulfonic acid (6.97 g, 30 mmol) in CH2Cl2 (10 ml) was added 3,4-dihydro-2H-pyran (20 ml) at rt and the reaction mixture was stirred for 14 h (in most cases, the reaction was completed after exothermic reaction subsided). The reaction mixture was diluted with CH2Cl2 (100 ml), washed with saturated NaHCO3 aqueous solution, dried (Na2SO4), and concentrated to give brown oil. This was purified by column chromatography (silica gel: 200 g, CH2Cl2 /MeOH: 40/1 as eluent) to give 8.78 g (97.6%) of desired compound as brown oil.

Workup

  1. customafter exothermic reaction
  2. washwashed with saturated NaHCO3 aqueous solution
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto give brown oil
  6. customThis was purified by column chromatography (silica gel: 200 g, CH2Cl2 /MeOH: 40/1 as eluent)

Sources & evidence

ORD record
ord-0200b72308964baba652aef4fe4d3a10
Source dataset
uspto-grants-2000_08
Patent number
US06110947

Reaction notes

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