Dimethylformamide → HCID 86738113, compound

HRID 1155371Notes

Reaction equation

HRID 1155371 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([C@@:10]23[CH2:19][C:18](=O)[CH2:17][CH2:16][C@@H:15]2[CH2:14][N:13]([CH3:21])[CH2:12][CH2:11]3)[CH:7]=[CH:8][CH:9]=1.[CH3:22]N(C)C=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:3][C:4]1[CH:5]=[C:6]([C@@:10]23[CH2:19][C:18](=[CH2:22])[CH2:17][CH2:16][C@@H:15]2[CH2:14][N:13]([CH3:21])[CH2:12][CH2:11]3)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 86738112HCID 86738112, compound

Product 1

HCID 86738113HCID 86738113, compound

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

3.93 g (11 mmol) of methyl triphenylphosphonium bromide in 100 ml of absolute dimethyl formamide is treated with 1.01 g of a 50% w/w sodium hydride dispersion in oil (21 mmol) under nitrogen. The mixture is stirred for 1 hour at room temperature, and then treated with 2.59 g of octahydro-4a-(3-hydroxyphenyl)-2-methyl-cis-6(2H)-isoquinolinone. The mixture is stirred for 16 hours at 40°, and partitioned between methylene chloride and aqueous ammonium sulphate. Evaporation of the organic phase and chromatographic purification on silicagel gives the title compound.

Workup

  1. stirringThe mixture is stirred for 16 hours at 40°
  2. custompartitioned between methylene chloride and aqueous ammonium sulphate
  3. customEvaporation of the organic phase and chromatographic purification on silicagel

Sources & evidence

ORD record
ord-ca0650f6cb024a0cbafbbdb843eb6354
Source dataset
uspto-grants-1981_11
Patent number
US04301290

Reaction notes

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