Iodoethane → HCID 57213539, compound

HRID 377441Notes

Reaction equation

HRID 377441 reaction equation
[NH2:1][C@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@H:3]1[OH:11].C(=O)([O-])[O-].[K+].[K+].[CH2:18](I)[CH3:19].[C:21](#N)[CH3:22]>C(OCC)C>[CH2:21]([N:1]([CH2:18][CH3:19])[C@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@H:3]1[OH:11])[CH3:22]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 9866743(1S,2R)-(-)-1-Amino-2-indanol

Product 1

HCID 57213539HCID 57213539, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A suspension of 15.09 grams (101 mmol) of (1S,2R)-1-amino-2-indanol, 33.72 grams (244 mmol) of potassium carbonate and 38.8 grams (249 mmol) of ethyl iodide in 100 ml of acetonitrile was refluxed for 3 hours. After cooling, the solid matter was removed through filtration and the filtrate was evaporated. The residue was dissolved in 4N hydrochloric acid and was washed three times using dichloromethane. The water layer was made basic with the aid of a 50% sodium hydroxide solution and was extracted with the aid of dichloromethane (3*25 ml). After drying (Na2SO4) and evaporation, the product was isolated as an oil. This oil was dissolved in diethyl ether and cooled, which caused the product to crystallise. Yield: 16.7 grams (81%) of a white solid substance. Melting point: 60-61° C. [α]20D +1.1 (c=1, methanol). 1H NMR (200 MHz, CDCl3): 1.02 (t, 6H), 2.24-2.57 (2*m, 4H), 2.65 (dd, 1H), 3.20 (dd, 1H), 4.22 (d, 1H), 4.29 (q, 1H), 4.7 (br s, 1H) and 7.10-7.27 (m, 4H). 13C NMR (50.31 MHz, CDCl3): 13.63 (q), 41.42 (t), 45.60 (t) 66.97 (d), 68.95 (d), 125.44 (d), 126.17 (d), 126.45 (d), 128.28 (d), 139.65(s) and 141.98 (s).

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperatureAfter cooling
  3. customthe solid matter was removed through filtration
  4. customthe filtrate was evaporated
  5. dissolutionThe residue was dissolved in 4N hydrochloric acid
  6. washwas washed three times
  7. extractionwas extracted with the aid of dichloromethane (3*25 ml)
  8. customAfter drying
  9. custom(Na2SO4) and evaporation
  10. customthe product was isolated as an oil
  11. temperaturecooled
  12. customto crystallise

Sources & evidence

ORD record
ord-45e0a8a87da0442682924f4ce974fe59
Source dataset
uspto-grants-2000_02
Patent number
US06025506

Reaction notes

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