Lithium Hydroxide → rac-(1R,2R)-2-(quinolin-6-yl)cyclopropane-1-carboxylic acid

HRID 655208Notes

Reaction equation

HRID 655208 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][CH:13]=[CH:12]2)=[O:5])C.[OH-].[Li+]>CO>[N:15]1[C:16]2[C:11](=[CH:10][C:9]([C@@H:7]3[CH2:8][C@H:6]3[C:4]([OH:5])=[O:3])=[CH:18][CH:17]=2)[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86641540trans 2-Quinolin-6-yl-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 86641541rac-(1R,2R)-2-(quinolin-6-yl)cyclopropane-1-carboxylic acidYield 91.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of trans 2-quinolin-6-yl-cyclopropanecarboxylic acid ethyl ester (125 mg, 0.523 mmol) in methanol (2 mL) was added 4 M aqueous solution of lithium hydroxide (0.65 mL, 2.62 mmol). The reaction mixture was stirred at room temperature for 3 h then it was concentrated in vacuo, diluted with water, and treated with 1 N aqueous hydrochloric acid until pH 4-5. The resulting precipitate was filtered, washed with water, and dried in vacuo to provide 102 mg of product as a white solid. 1H NMR 500 MHz (DMSO) δ 1.50 (m, 2H), 1.96 (m, 1H), 2.60 (m, 1H), 7.50 (dd, 1H), 7.57 (dd, 1H), 7.78 (d, 1H), 7.93 (d, 1H), 8.26 (dd, 1H), 8.83 (dd, 1H); MS (m/z) 214 [M+H+]+.

Workup

  1. concentrationit was concentrated in vacuo
  2. additiondiluted with water
  3. additiontreated with 1 N aqueous hydrochloric acid until pH 4-5
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-32e7e85aa9ea44888d4656779a6d42e6
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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