Potassium Carbonate → HCID 68511182, compound

HRID 1716583Notes

Reaction equation

HRID 1716583 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.[C:13](=[O:20])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[NH2:14].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.[Cu]I>[C:16]([O:15][C:13](=[O:20])[NH:14][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)([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 77922tert-Butyl carbamate2×HCID 68507957HCID 68507957, compound

Product 1

HCID 68511182HCID 68511182, compoundYield 24.4%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst2×HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

((S)-5-Bromo-indan-2-yl)-methanol (1.45 g, 6.38 mmol) was dissolved in toluene (12 mL) and argon gas bubbled through the solution for 10 minutes. To the stirring mixture was added, in the following order: tert-butyl carbamate (1.25 g, 10.67 mmol), copper(I) iodide (255 mg, 1.33 mmol), K2 CO3 (2.46 g, 17.8 mmol) and finally N,N′-dimethylethylene-1,2-diamine (285 μL, 2.61 mmol). The mixture was mechanically stirred under argon at 110° C. After 18 hours, tlc monitoring of the reaction showed remaining starting material, the following additional reagents were added: tert-butyl carbamate (125 mg, 1.06 mmol), copper(I) iodide (25 mg, 0.13 mmol), potassium carbonate (250 mg, 1.8 mmol) and N,N′-dimethylethylene-1,2-diamine (30 μL, 0.27 mmol). Heating at 110° C. was continued for 2 hours after which the reaction mixture was cooled, solids removed by filtration and the filtrate evaporated, dissolved in a minimum amount of CH2Cl2 and purified by flash chromatography (ethyl ether). A crude product was obtained which was crystallized from 1:1 diethyl ether:hexane to give ((S)-2-Hydroxymethyl-indan-5-yl)-carbamic acid tert-butyl ester (410 mg, 24%) of white crystals. The mother liquor, comprised of a mixture of desired product and starting material was reserved to be reacted again.

Workup

  1. customargon gas bubbled through the solution for 10 minutes
  2. additionTo the stirring mixture was added, in the following order
  3. additionthe following additional reagents were added
  4. temperatureHeating at 110° C.
  5. waitwas continued for 2 hours
  6. temperatureafter which the reaction mixture was cooled
  7. customsolids removed by filtration
  8. customthe filtrate evaporated
  9. dissolutiondissolved in a minimum amount of CH2Cl2
  10. custompurified by flash chromatography (ethyl ether)
  11. customA crude product was obtained which
  12. customwas crystallized from 1:1 diethyl ether

Sources & evidence

ORD record
ord-cdfc4efc870d4878a07e7ffbb208cebd
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

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