HCID 25241852, compound → HCID 25241888, compound

HRID 2406861Notes

Reaction equation

HRID 2406861 reaction equation
[CH2:1]([O:3][C:4](=[O:19])/[C:5](/[CH3:18])=[CH:6]/[C@@H:7]1[CH2:15][CH2:14][C:13]([CH3:16])=[C:12]2[C@@H:8]1[C@@H:9]([OH:17])[CH2:10][CH2:11]2)[CH3:2].[H][H]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:19])/[C:5](/[CH3:18])=[CH:6]/[C@@H:7]1[CH2:15][CH2:14][C@@H:13]([CH3:16])[C@@H:12]2[C@@H:8]1[C@@H:9]([OH:17])[CH2:10][CH2:11]2)[CH3:2]

Participants

4

Reactant 2

HCID 25241852HCID 25241852, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 25241888HCID 25241888, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of compound (10a) (223.8 mg, 0.8466 mmol) and degassed DCM (34) was cooled to 0° C. The flask was flushed with hydrogen over a period of 2 minutes before hydrogen was bubbled through the solution itself for one additional minute. After adding Crabtree catalyst (68.0 mg, 0.0845 mmol) the flask was once again flashed with hydrogen for 3 minutes before hydrogen was bubbled through the solution for 2 minutes until it became colorless. The icebath was removed and the mixture stirred for 2¼ hours. Argon was bubbled through the reaction mixture and the solvent was evaporated. Chromatography (hexane/EtOAc 7/1 to 3/1) of the residue furnished 162.7 mg of compound of (11a) as white solid with 72% yield.

Workup

  1. customThe flask was flushed with hydrogen over a period of 2 minutes before hydrogen
  2. customwas bubbled through the solution itself for one additional minute
  3. customwas bubbled through the solution for 2 minutes until it
  4. customThe icebath was removed
  5. customArgon was bubbled through the reaction mixture
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6573002997ee4528bb8386f35965a0fc
Source dataset
uspto-grants-2014_08
Patent number
US08809395B2

Reaction notes

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