Lithium hydroxide, monohydrate → HCID 59300474, compound

HRID 603443Notes

Reaction equation

HRID 603443 reaction equation
[CH2:1]([C:3]1[N:8]=[C:7]([CH3:9])[C:6]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[C@H:20]([CH2:24][C:25]([O:27]C)=[O:26])[CH2:19][CH2:18]3)=[CH:5][CH:4]=1)[CH3:2].O[Li].O>C1COCC1.CO.O>[CH2:1]([C:3]1[N:8]=[C:7]([CH3:9])[C:6]([O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[C@H:20]([CH2:24][C:25]([OH:27])=[O:26])[CH2:19][CH2:18]3)=[CH:5][CH:4]=1)[CH3:2]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59300455HCID 59300455, compound

Product 1

HCID 59300474HCID 59300474, compoundYield 16%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl ((1S)-5-{3-[(6-ethyl-2-methyl-3-pyridinyl)oxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate (Example 246) in a mixture of THF (3 mL) and MeOH (˜0.2 mL), was added LiOH.H2O (15 mg, 0.36 mmol) in water (1 mL). The mixture was stirred for 12 h at rt, the solvents were evaporated, and the residue was suspended in a small volume of water. The aqueous solution was acidified to pH<3 using HCl (1 N aqueous solution), and then it was extracted with excess EtOAc. The organic layer was dried, concentrated and purified by preparative HPLC to give 18 mg (16%) of the product as a solid. 1H NMR (400 MHz, CDCl3): δ 7.16-6.88 (m, 3H), 6.71 (s, 1H), 6.62 (dd, 1H), 4.12-4.0 (m, 4H), 3.52-3.40 (m, 1H), 2.90-2.62 (m, 6H), 2.52-2.26 (m, 4H), 2.23-2.12 (m, 2H), 1.78-1.64 (m, 1H), 1.08 (t, 3H).

Workup

  1. customthe solvents were evaporated
  2. extractionit was extracted with excess EtOAc
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-f815a5beded7458ea19615b214bf79b1
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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