HCID 20638810, compound → HCID 20638811, compound

HRID 1276515Notes

Reaction equation

HRID 1276515 reaction equation
[C:1]1([C@@H:7]2[CH:12]=[CH:11][CH2:10][CH2:9][C@@H:8]2[C:13](OC)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl.C1(C)C=CC=CC=1>[C:1]1([C@@H:7]2[CH:12]=[CH:11][CH2:10][CH2:9][C@@H:8]2[CH2:13][OH:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 20638810HCID 20638810, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 20638811HCID 20638811, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 300 mg (1.38 mmol) of 1(R)-phenyl-2(S)-carbomethoxy-cyclohex-5-ene (from Step A) in 30 mL of CH2Cl2 at 0° C. was treated with 2.3 mL of 1.5 M diisobutylaluminum hydride solution in toluene. After stirring for 30 minutes the reaction was quenched with 50 mL of sat'd sodium potassium tartrate solution, diluted with 100 mL of ether and stirred at rt for 20 h. The layers were separated and the organic layer was washed with 75 mL of H2O , dried over MgSO4 and concentrated in vacuo. Flash chromatography on 100 g of silica gel using 5-25% v/v EtOAc/hexanes as the eluant afforded 185 mg (72%) of the title compound as an oil. 1H NMR (CDCl3, 500 MHz) δ 7.23-7.34 (m, 5H), 5.95-5.97 (m, 1H), 5.77-5.79 (m, 1H),3.66 (s, 1H), 3.23-3.32 (m, 2H), 2.14-2.25 (m, 3H),1.51-1.62 (m, 3H) ppm.

Workup

  1. customwas quenched with 50 mL of sat'd sodium potassium tartrate solution
  2. additiondiluted with 100 mL of ether
  3. stirringstirred at rt for 20 h
  4. customThe layers were separated
  5. washthe organic layer was washed with 75 mL of H2O
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3d828cf3cd47402ca1dd78cefda8558a
Source dataset
uspto-grants-2000_12
Patent number
US06166037

Reaction notes

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