Methanol → HCID 58697560, compound

HRID 2212974Notes

Reaction equation

HRID 2212974 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:10][CH2:9][CH2:8][C@@H:7]1[C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[C:20]#[N:21])=[O:5])C.O.[OH-].[Li+].CO>O>[C:20]([C:14]1[C:13]2[C:17](=[CH:18][CH:19]=[C:11]([C@@H:7]3[CH2:8][CH2:9][CH2:10][C@H:6]3[C:4]([OH:5])=[O:3])[CH:12]=2)[NH:16][CH:15]=1)#[N:21]

Participants

5

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 69659045HCID 69659045, compound

Product 1

HCID 58697560HCID 58697560, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of cis-2-(3-Cyano-1H-indol-5-yl)-cyclopentanecarboxylic acid ethyl ester (0.95 g, 3.36 mMol), lithium hydroxide monohydrate (0.71 g, 16.8 mMol), methanol (20 mL), and water (5 mL) was heated at reflux for 6 h. The solution was concentrated in vacuo and the residue dissolved in water and washed once with dichloromethane. The aqueous layer was acidified with concentrated hydrochloric acid and extracted with ethyl acetate (3×20 mL). The pooled organic extracts were washed once with brine, dried over sodium sulfate, and concentrated in vacuo to give the product as a light brown oil which solidified upon standing (0.66 g, 77%). LC-MS: 1.33 min (2 min gradient); 277.07 (MNa)+.

Workup

  1. temperatureat reflux for 6 h
  2. concentrationThe solution was concentrated in vacuo
  3. dissolutionthe residue dissolved in water
  4. washwashed once with dichloromethane
  5. extractionextracted with ethyl acetate (3×20 mL)
  6. washThe pooled organic extracts were washed once with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-05778a1793254296bf04f04095071687
Source dataset
uspto-grants-2006_09
Patent number
US07105516B2

Reaction notes

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