Spiro[3.3]heptane-2-carboxylic acid, 6,6-difluoro-, phenylmethyl ester → 6,6-Difluoro-spiro[3.3]heptane-2-carboxylic acid

HRID 520378Notes

Reaction equation

HRID 520378 reaction equation
[F:1][C:2]1([F:19])[CH2:18][C:4]2([CH2:7][CH:6]([C:8]([O:10]CC3C=CC=CC=3)=[O:9])[CH2:5]2)[CH2:3]1>[Pd].CCOC(C)=O>[F:1][C:2]1([F:19])[CH2:3][C:4]2([CH2:7][CH:6]([C:8]([OH:10])=[O:9])[CH2:5]2)[CH2:18]1

Participants

4

Reactant 1

HCID 86690095Spiro[3.3]heptane-2-carboxylic acid, 6,6-difluoro-, phenylmethyl ester

Product 1

HCID 717439746,6-Difluoro-spiro[3.3]heptane-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A stirred suspension of 10% Pd—C (40.6 mg) in an EtOAc (10 mL) solution of benzyl 6,6-difluorospiro[3.3]heptane-2-carboxylate (203 mg) was hydrogenated under balloon pressure for 2 h. The suspension was filtered and the filtrate was evaporated to dryness to afford Cap-13 as a clear viscous oil. 1H NMR (400 MHz, CHLOROFORM-d) δ 3.18-3.08 (m, 1H), 2.69-2.55 (m, 4H), 2.52-2.37 (m, 4H).

Workup

  1. filtrationThe suspension was filtered
  2. customthe filtrate was evaporated to dryness
  3. customto afford Cap-13 as a clear viscous oil

Sources & evidence

ORD record
ord-01a48a4e36624f30a3e8d42f75754817
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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