HCID 71744042, compound → HCID 71743923, compound

HRID 520376Notes

Reaction equation

HRID 520376 reaction equation
[F:1][C:2]1([F:20])[CH2:9][CH:8]2[CH:4]([CH2:5][CH:6]([C:10]([O:12]CC3C=CC=CC=3)=[O:11])[CH2:7]2)[CH2:3]1>CCOC(C)=O.[Pd]>[F:1][C:2]1([F:20])[CH2:3][CH:4]2[CH:8]([CH2:7][CH:6]([C:10]([OH:12])=[O:11])[CH2:5]2)[CH2:9]1

Participants

4

Reactant 1

HCID 71744042HCID 71744042, compound

Product 1

HCID 71743923HCID 71743923, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A stirred suspension of 10% Pd—C (12.53 mg) in a solution of benzyl 5,5-difluorooctahydropentalene-2-carboxylate (33 mg) in EtOAc (5 mL) was hydrogenated under balloon pressure for 2-3 h. The suspension was filtered and evaporated to dryness to afford a mixture of endo/exo isomers of Cap-12 as a white semi-solid. 1H NMR (400 MHz, chloroform-d) δ 3.04-2.93 (m, 1H), 2.88-2.76 (m, 2H), 2.40-2.26 (m, 2H), 2.15-2.04 (m, 2H), 1.87-1.71 (m, 4H).

Workup

  1. filtrationThe suspension was filtered
  2. customevaporated to dryness
  3. customto afford
  4. additiona mixture of endo/exo isomers of Cap-12 as a white semi-solid

Sources & evidence

ORD record
ord-0c30cfc5ee66481380fa875d5d6f09af
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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