Dimethylformamide → HCID 68512326, compound

HRID 1716586Notes

Reaction equation

HRID 1716586 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@H:6]([CH2:11][OH:12])[CH2:5]2.[CH3:13][N:14](C=O)C>[C-]#N.[Zn+2].[C-]#N>[C:13]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@H:6]([CH2:11][OH:12])[CH2:5]2)#[N:14]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 68507957HCID 68507957, compound

Product 1

HCID 68512326HCID 68512326, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Conditions

Temperature
175 °C

Procedure

The (S)-5-bromoindan-2-yl-methanol (600 mg, 2.64 mmol) was mixed with zinc cyanide (480 mg, 4.09 mmol) in DMF (15 mL). To this solution was added palladium tetrakistriphenylphosphine (180 mg, 0.15 mmol). The mixture was heated in a microwave at 175° C. for 20 minutes. Solvents were evaporated and the residue was extracted with ethyl acetate and 0.1N hydrochloric acid. The organic layer was washed with brine and dried over Na2SO4. Solvents were evaporated and the residue was purified through a Biotage flash column chromatography using hexanes and ethyl acetate (2:1 to 1:1 ratio) to give (S)-5-cyanoindan-2-yl-methanol as a colorless oil (357 mg, 78%). Chiral HPLC analysis indicated no racemization.

Workup

  1. customSolvents were evaporated
  2. extractionthe residue was extracted with ethyl acetate and 0.1N hydrochloric acid
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customSolvents were evaporated
  6. customthe residue was purified through a Biotage flash column chromatography

Sources & evidence

ORD record
ord-f634d3b6b16b4ed099907c5853c7dfd9
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

Loading…