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

HRID 1193290Notes

Reaction equation

HRID 1193290 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

(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)

Workup

  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

Sources & evidence

ORD record
ord-4a2ee615d7b94696b09379bed307f510
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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