Sodium Cyanide → HCID 15374516, compound

HRID 1019271Notes

Reaction equation

HRID 1019271 reaction equation
[Li][C:2]#[N:3].C1(C)C=CC(S(O[CH2:14][C@H:15]([OH:26])[CH2:16][C:17]2[NH:18][C:19]3[C:24]([CH:25]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3)(=O)=O)=CC=1.[C-]#N.[Na+]>CN(C=O)C>[OH:26][C@H:15]([CH2:16][C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14][C:2]#[N:3]

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 53647276(R)-3-indol-2-yl-2-hydroxypropanyl p-toluenesulfonateHCID 178506913HCID 178506913, compound

Product 1

HCID 15374516HCID 15374516, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 0.5 M LiCN in DMF (30 mL) was added (R)-3-indol-2-yl-2-hydroxypropanyl p-toluenesulfonate (R)-2 (5.6 g, 16.2 mmol) and sodium cyanide (1.5 g, 30.6 mmol). The reaction mixture was stirred for 1 hour at 100° C., cooled to room temperature, poured into 80 mL ice-water, and extracted with ethyl acetate (3×50 mL). The combined organic solution was washed with saturated sodium bicarbonate (2×50 mL), brine (2×30 mL), dried over anhydrous sodium sulfate, and evaporated to yield a deep red oil. The oil was purified by flash chromatography (hexane:ethyl acetate 2:3) to give 2.4 g (74%) of the title compound as a light yellow solid.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe combined organic solution was washed with saturated sodium bicarbonate (2×50 mL), brine (2×30 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customto yield a deep red oil
  7. customThe oil was purified by flash chromatography (hexane:ethyl acetate 2:3)

Sources & evidence

ORD record
ord-d746a538be4c40b0bd8f3df93b2ce5c4
Source dataset
uspto-grants-2002_11
Patent number
US06486313B1

Reaction notes

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