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Lithium hydroxide, monohydrate → (R)-3-(3-Cyclopentyl-N-methylpropanamido)-2,3-dihydro-1H-indene-5-carboxylic acid

HRID 1193290
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1193290
[CH:1]1([CH2:6][CH2:7][C:8]([N:10]([C@H:12]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:21]([O:23]C)=[O:22])[CH:19]=3)[CH2:14][CH2:13]2)[CH3:11])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.O[Li].O>CO.C1COCC1.O>[CH:1]1([CH2:6][CH2:7][C:8]([N:10]([C@H:12]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:21]([OH:23])=[O:22])[CH:19]=3)[CH2:14][CH2:13]2)[CH3:11])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1
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Komponenten

4

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 66805313(R)-Methyl 3-(3-cyclopentyl-N-methylpropanamido)-2,3-dihydro-1H-indene-5-carboxylate

Produkt 1

HCID 66798592(R)-3-(3-Cyclopentyl-N-methylpropanamido)-2,3-dihydro-1H-indene-5-carboxylic acidAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

(R)-Methyl 3-(3-cyclopentyl-N-methylpropanamido)-2,3-dihydro-1H-indene-5-carboxylate (B-80) (1.5 g, 4.56 mmol, 1.0 eq.) was dissolved in MeOH:THF:H2O (1:1:1, 24 ml); LiOH H2O (383 mg, 9.118 mmol, 2.0 eq.) was added at 0° C., and the mixture was stirred for 4 hours at RT. After monitoring by TLC, the reaction solution was concentrated under reduced pressure, and the residue was taken up in water (15 ml) and extracted with ethyl acetate (2×20 ml). The aqueous phase was adjusted to pH 1-2 with 3 M HCl solution and extracted with DCM (3×50 ml). The combined org. phases were washed with sat. NaCl solution (50 ml), dried over sodium sulfate and concentrated under reduced pressure, dried. The crude product was used in the next stage without being purified further. Yield: 83% (1.2 g, 0.415 mmol)

Aufarbeitung

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate (2×20 ml)
  3. extractionextracted with DCM (3×50 ml)
  4. washphases were washed with sat. NaCl solution (50 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customdried
  8. customwithout being purified further

Quellen und Nachweise

ORD-Eintrag
ord-4a2ee615d7b94696b09379bed307f510
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08680159B2

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