Lithium Hydroxide → 5-(1-((Tert-butoxy)carbonyl)pyrrolidin-2-yl)thiophene-2-carboxylic acid

HRID 564230Notes

Reaction equation

HRID 564230 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]([CH:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:7][CH:6]=1)=[O:4].[OH-].[Li+]>C1COCC1.O>[C:18]([O:17][C:15]([N:11]1[CH2:12][CH2:13][CH2:14][CH:10]1[C:8]1[S:9][C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 66758891Tert-butyl 2-(5-(methoxycarbonyl)thiophen-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 667594265-(1-((Tert-butoxy)carbonyl)pyrrolidin-2-yl)thiophene-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of EXAMPLE 34B (2.7 g) in THF (50 mL) was added lithium hydroxide (0.2 g) in water (5 mL). The mixture was stirred at ambient temperature overnight and partitioned between ethyl acetate and 0.5 M hydrochloric acid. The extract was washed with water, dried over magnesium sulfate, filtered and concentrated. The concentrate was flash chromatographed on silica gel with ethyl acetate.

Workup

  1. custompartitioned between ethyl acetate and 0.5 M hydrochloric acid
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-4de8ae4456854767ba8f8dfdece1e3d3
Source dataset
uspto-grants-2011_11
Patent number
US08067613B2

Reaction notes

Loading…