Lithium Hydroxide → (2S,4R)-1-{[(2-methyl-2-propanyl)oxy]carbonyl}-4-[1-(methylsulfonyl)-4-piperidinyl]-2-pyrrolidinecarboxylic acid

HRID 1053832Notes

Reaction equation

HRID 1053832 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH:13]2[CH2:18][CH2:17][N:16]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:15][CH2:14]2)[CH2:10][C@H:9]1[C:23]([O:25]C)=[O:24])=[O:7])([CH3:4])[CH3:3].[OH-].[Li+]>O1CCCC1.O>[CH3:4][C:2]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH:13]2[CH2:18][CH2:17][N:16]([S:19]([CH3:22])(=[O:20])=[O:21])[CH2:15][CH2:14]2)[CH2:10][C@H:9]1[C:23]([OH:25])=[O:24])=[O:7])([CH3:1])[CH3:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 122584918methyl (2S,4R)-1-{[(2-methyl-2-propanyl)oxy]carbonyl}-4-[1-(methylsulfonyl)-4-piperidinyl]-2-pyrrolidinecarboxylate

Product 1

HCID 118107723(2S,4R)-1-{[(2-methyl-2-propanyl)oxy]carbonyl}-4-[1-(methylsulfonyl)-4-piperidinyl]-2-pyrrolidinecarboxylic acidYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound prepared in Example 62 (2.87 g, 7.36 mmol) in tetrahydrofuran (20 mL) and water (20 mL) at 0° C. was added lithium hydroxide (0.35 g, 14.7 mmol). The reaction was warmed to room temperature and stirred overnight whereupon it was partitioned between methyl tert-butyl ether and water. The aqueous layer was separated and carefully acidified to pH 1 with 6 N hydrochloric acid. The aqueous solution was extracted with ethyl acetate (2×300 mL) and the combined organic extracts concentrated to give the title compound (2.35 g, 85%) as a white solid.

Workup

  1. customwas partitioned between methyl tert-butyl ether and water
  2. customThe aqueous layer was separated
  3. extractionThe aqueous solution was extracted with ethyl acetate (2×300 mL)
  4. concentrationthe combined organic extracts concentrated

Sources & evidence

ORD record
ord-f259df4750034cf488cb67bf7b6615a6
Source dataset
uspto-grants-2016_07
Patent number
US09394250B2

Reaction notes

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