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

HRID 520378Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 520378
[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

Komponenten

4

Edukt 1

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-01a48a4e36624f30a3e8d42f75754817
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09326973B2

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