Lithium hydroxide, monohydrate → HCID 59735066, compound

HRID 746413Notes

Reaction equation

HRID 746413 reaction equation
[CH:1]([C@:4]1([C:17]([O:19]C)=[O:18])[CH2:8][CH2:7][C@@H:6]([N:9]([CH3:16])[CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH2:5]1)([CH3:3])[CH3:2].C1COCC1.CO.O[Li].O>O>[CH:1]([C@:4]1([C:17]([OH:19])=[O:18])[CH2:8][CH2:7][C@@H:6]([N:9]([CH3:16])[CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH2:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 21899815MeOH tetrahydrofuranHCID 59734975HCID 59734975, compound

Product 1

HCID 59735066HCID 59735066, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of methyl (1S,3R)-1-isopropyl-3-[methyl(tetrahydro-2H-pyran-4-yl)amino]cyclopentanecarboxylate (1.0 g, 3.5 mmol) in 1:1 THF/MeOH (20 mL) was treated with a solution of LiOH.H2O (735 mg) in 10 mL of water. After several hours very little hydrolysis was observed by HPLC-MS analysis so the reaction mixture was warmed to reflux and stirred for 2 days. The pH of the reaction mixture was then adjusted to 7 and the mixture was concentrated. The residue was suspended in 50% methanol/DCM, filtered, and the filtrate was concentrated to afford 900 mg of (1S,3R)-1-isopropyl-3-[methyl(tetrahydro-2H-pyran-4-yl)amino]cyclopentanecarboxylic acid which required no further purification.

Workup

  1. customAfter several hours very little hydrolysis
  2. temperaturewas warmed
  3. temperatureto reflux
  4. concentrationthe mixture was concentrated
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5eab68cdb7064f2da3dcc99a712661db
Source dataset
uspto-grants-2008_07
Patent number
US07393844B2

Reaction notes

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