Methanol → (2E,4E)-4-(1-(Benzo[d][1,3]dioxol-5-ylmethyl)pyrrolidin-3-ylidene)but-2-enoic acid

HRID 1907747Notes

Reaction equation

HRID 1907747 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]3[CH2:15][CH2:14]/[C:13](=[CH:16]\[CH:17]=[CH:18]\[C:19]([O:21]CC)=[O:20])/[CH2:12]3)=[CH:9][C:4]=2[O:3][CH2:2]1.C1COCC1.CO.[OH-].[Li+]>O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]3[CH2:15][CH2:14]/[C:13](=[CH:16]\[CH:17]=[CH:18]\[C:19]([OH:21])=[O:20])/[CH2:12]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 59737265(2E,4E)-Ethyl 4-(1-(benzo[d][1,3]dioxol-5-ylmethyl)pyrrolidin-3-ylidene)but-2-enoate

Product 1

HCID 59737348(2E,4E)-4-(1-(Benzo[d][1,3]dioxol-5-ylmethyl)pyrrolidin-3-ylidene)but-2-enoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of ester 275 (0.15 g, 0.485 mmol) in 2:1 THF:MeOH (6 mL) was treated with a solution of lithium hydroxide (59 mg, 1.41 mmol) in H2O (3 mL) and stirred for 18 h. The reaction mixture was quenched with 1N HCl (2.0 mL), concentrated, diluted with H2O, cooled to −78° C. and lyophilized to provide title compound 276 (quantitative, in a mixture with LiCl).

Workup

  1. customThe reaction mixture was quenched with 1N HCl (2.0 mL)
  2. concentrationconcentrated
  3. additiondiluted with H2O

Sources & evidence

ORD record
ord-92d5f264282744acb69bd5daad313487
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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