Hydrochloric Acid → HCID 90200269, compound

HRID 516201Notes

Reaction equation

HRID 516201 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)[CH:9]=[CH2:10])(C)(C)C.Cl>CO.O1CCOCC1>[Cl:17][C:13]1[CH:12]=[C:11]([C@@H:8]([NH2:7])[CH:9]=[CH2:10])[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131733333HCID 131733333, compound

Product 1

HCID 90200269HCID 90200269, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

(S)-tert-Butyl(1-(3-chlorophenyl)allyl)carbamate: To a solution of Intermediate 9A (1.38 g, 5.08 mmol) in MeOH (10 mL) was added 4 N HCl (6.35 mL, 25.4 mmol) in dioxane and the resulting reaction was stirred at rt for 1 h. After this time, the reaction mixture was concentrated and coevaporated with toluene (2×). The crude product was then triturated with ether, filtered and washed with additional ether to give (S)-1-(3-chlorophenyl)prop-2-en-1-amine (0.8 g, 94%) as a beige solid. MS (ESI) m/z: 150.8 (M+H—NH3)+. The beige solid was dissolved in ACN (25 mL) and TEA (4 mL, 28.7 mmol) and to this solution was added Boc2O (1.415 mL, 6.09 mmol). The reaction mixture was stirred at rt overnight. The reaction mixture was diluted with EtOAc and washed with water followed by brine. The crude product was then purified by silica gel chromatography to give the desired product, Intermediate 9B (546 mg, 40%) as a clear oil. MS(ESI) m/z: 290.0 (M+Na)+.

Workup

  1. customthe resulting reaction
  2. concentrationAfter this time, the reaction mixture was concentrated
  3. customThe crude product was then triturated with ether
  4. filtrationfiltered
  5. washwashed with additional ether

Sources & evidence

ORD record
ord-3e86706669894b2e9c54092ca96949f1
Source dataset
uspto-grants-2015_08
Patent number
US09108981B2

Reaction notes

Loading…