Lithium hydroxide, monohydrate → HCID 57437882, compound

HRID 2081125Notes

Reaction equation

HRID 2081125 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([C:11]([O:13][C@H:14]1[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@H:16]([C:26]([O:28]C)=[O:27])[CH2:15]1)=[O:12])[CH2:6]2.O[Li].O>C1COCC1.CO.O>[C:22]([O:21][C:19]([N:17]1[CH2:18][C@H:14]([O:13][C:11]([N:5]2[CH2:4][C:3]3[C:7](=[CH:8][CH:9]=[CH:10][C:2]=3[Cl:1])[CH2:6]2)=[O:12])[CH2:15][C@H:16]1[C:26]([OH:28])=[O:27])=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57692649HCID 57692649, compound2×

Product 1

HCID 57437882HCID 57437882, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

This ester product, (2S,4R)-1-tert-butyl 2-methyl 4-(4-chloroisoindoline-2-carbonyloxy)pyrrolidine-1,2-dicarboxylate (0.78 g, 1.8 mmol) was then dissolved in a mixture of solvent THF:MeOH:water 2:2:1 (v/v) (5.4 mL), followed by addition of LiOH—H2O (0.15 g, 3.7 mmol). After stirring at rt for overnight, the reaction was concentrated to near dryness. The resulting solid residue was re-dissolved in water (40 mL) and washed with ether (2×30 mL). The aqueous layer was acidified with 1N HCl to pH ˜2 and the combined EtOAc extracts (3×30 mL) was washed with brine and dried (Na2SO4), giving the titled product as a white foamy solid after evaporation of solvent.

Workup

  1. concentrationthe reaction was concentrated
  2. dissolutionThe resulting solid residue was re-dissolved in water (40 mL)
  3. washwashed with ether (2×30 mL)
  4. washwas washed with brine
  5. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-3ef65ebc249043b79be4beedd97a4b5a
Source dataset
uspto-grants-2011_04
Patent number
US07932277B2

Reaction notes

Loading…