Dimethylamine → HCID 23518920, compound

HRID 1836616Notes

Reaction equation

HRID 1836616 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:7]=[C:6]2[C@H:22]1[CH2:24][C@H:23]1[CH:25]=O)#[N:2].[CH3:27][NH:28][CH3:29].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)C>[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:7]=[C:6]2[C@H:22]1[CH2:24][C@H:23]1[CH2:25][N:28]([CH3:29])[CH3:27])#[N:2]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 11559623HCID 11559623, compound

Product 1

HCID 23518920HCID 23518920, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the crude cis-2-[5-Cyano-1-(p-toluenesulfonyl)indol-3-yl]cyclopropanecarboxaldehyde, dimethylamine (0.35 ml, 0.7 mmol, 2.0 M/THF), and anhydrous ethanol (10 ml) was heated with stirring until all solids were dissolved. The reaction vessel was removed from the heating source and sodium triacetoxyborohydride (300 mg, 1.41 mmol) was added. After stirring for 1 h, the solvent was evaporated. The residue was taken up in brine (10 ml) and aqueous 1N sodium hydroxide was added until solids disappeared. The aqueous layer was extracted with ethyl acetate ((4×10 ml), dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the crude cis-2-[5-cyano-1-(p-toluenesulfonyl)indol-3-yl]-1-(N,N-dimethylaminomethyl)cyclopropane.

Workup

  1. temperaturewas heated
  2. dissolutionwere dissolved
  3. additionwas added
  4. stirringAfter stirring for 1 h
  5. customthe solvent was evaporated
  6. additionaqueous 1N sodium hydroxide was added until solids
  7. extractionThe aqueous layer was extracted with ethyl acetate ((4×10 ml)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8f44de28aa1b47adbacbdc47367197aa
Source dataset
uspto-grants-2004_08
Patent number
US06777437B2

Reaction notes

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