Dimethylformamide → HCID 59104142, compound

HRID 899385Notes

Reaction equation

HRID 899385 reaction equation
C([O-])([O-])=O.[K+].[K+].[C:7]1(=[O:17])[NH:11][C:10](=[O:12])[C:9]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:8]12.CN(C=O)C.Br[CH2:24][C:25]1[CH2:30][CH2:29][C@H:28]([C:31]([OH:34])([CH3:33])[CH3:32])[CH2:27][CH:26]=1>O>[OH:34][C:31]([C@H:28]1[CH2:29][CH2:30][C:25]([CH2:24][N:11]2[C:7](=[O:17])[C:8]3[C:9](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:10]2=[O:12])=[CH:26][CH2:27]1)([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6809PhthalimideHCID 11430Potassium CarbonateHCID 10955451HCID 10955451, compound

Product 1

HCID 59104142HCID 59104142, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.2 g (16 mmol) K2CO3, 1.2 g (8.4 mmol) phthalimide, and 40 ml DMF was stirred at room temperature for 0.5 hours. Thereafter, 1.7 g (7.4 mmol) (S)-2-(4-bromomethyl-cyclohex-3-enyl)-propan-2-ol (Bull, et. al. Aust. J. Chem., 46 1869, 1993) was added and the resulting mixture was stirred at room temperature for 72 h. Water was added and the mixture was then extracted with ethyl acetate. The ethyl acetate extracts were combined; washed with water and brine; dried (MgSO4); and filtered and concentrated in vacuo. Chromatography on silica gel using 20% ethyl acetate/hexanes yielded 0.62 g (28%) of the desired product.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 72 h
  2. extractionthe mixture was then extracted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationand filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f20cebcdccd044a78870854fc0456ba3
Source dataset
uspto-grants-2008_04
Patent number
US07354941B2

Reaction notes

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