3,4-dihydro-2H-pyran → HCID 18391989, compound

HRID 618280Notes

Reaction equation

HRID 618280 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>C(Cl)Cl>[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

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 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 6344DichloromethaneSolvent2×

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 tas 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 tas purified by column chromatography (silica gel:200 g, CH2Cl2 /MeOH:40/1 as eluent)

Sources & evidence

ORD record
ord-78637cfff7644dd982b9f85acf4d6edf
Source dataset
uspto-grants-1999_09
Patent number
US05952369

Reaction notes

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