Sodium → HCID 69658454, compound

HRID 2212969Notes

Reaction equation

HRID 2212969 reaction equation
[Na].[CH2:2]([O:4][C:5]([C@@H:7]1[CH2:11][CH2:10][CH2:9][C@@H:8]1[C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:21]#[N:22])[CH:19]=2)[NH:14][CH:13]=1)=[O:6])C>CO>[CH3:2][O:4][C:5]([C@@H:7]1[CH2:11][CH2:10][CH2:9][C@H:8]1[C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:21]#[N:22])[CH:19]=2)[NH:14][CH:13]=1)=[O:6]

Participants

4

Reactant 2

HCID 5360545SodiumHCID 69658351HCID 69658351, compound

Product 1

HCID 69658454HCID 69658454, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium metal (13.5 g, 556 mMol) was carefully added portion-wise to anhydrous methanol (400 mL). A solution of cis-2-(5-cyanoindol-3-yl)-cyclopentanecarboxylic acid ethyl ester (33.1 g, 117 mMol) in methanol (100 mL) was added over 5 minutes. The mixture was heated at a gentle reflux for 18 hours, carefully quenched with water, and evaporated in vacuo. The residue was dissolved ethyl acetate (600 mL), washed with saturated sodium chloride (100 mL), dried over sodium sulfate, and concentrated in vacuo to give the product as an 88:12 cis/trans diastereomeric mixture which was used without further purification (27 g, 86%).

Workup

  1. temperatureThe mixture was heated at
  2. temperaturea gentle reflux for 18 hours
  3. customcarefully quenched with water
  4. customevaporated in vacuo
  5. dissolutionThe residue was dissolved ethyl acetate (600 mL)
  6. washwashed with saturated sodium chloride (100 mL)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customto give the product as an 88:12 cis/trans diastereomeric mixture which
  10. customwas used without further purification (27 g, 86%)

Sources & evidence

ORD record
ord-6aed4c6f273e4ab68f4d3c79db84bba7
Source dataset
uspto-grants-2006_09
Patent number
US07105516B2

Reaction notes

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