Hydrochloric Acid → HCID 55278056, compound

HRID 516200Notes

Reaction equation

HRID 516200 reaction equation
C(OC(=O)[NH:7][C@@H:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:12]=1[F:18])[CH:9]=[CH2:10])(C)(C)C.Cl>CO>[Cl:17][C:13]1[C:12]([F:18])=[C:11]([C@H:8]([NH2:7])[CH:9]=[CH2:10])[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131733332HCID 131733332, compound

Product 1

HCID 55278056HCID 55278056, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-tert-Butyl(1-(3-chloro-2-fluorophenyl)allyl)carbamate: To a solution of crude Intermediate 6B (1.44 g, 4.97 mmol) in MeOH (10 mL) was added HCl (7 mL, 28.0 mmol) and stirred at rt for 1 h. Aliquot LCMS indicates that the starting material had been consumed. The reaction mixture was concentrated and coevaporated with toluene (2×). The crude product was then triturated with ether, filtered and then washed with ether to give (R)-1-(3-chloro-2-fluorophenyl)prop-2-en-1-amine as beige solid. The solid was dissolved in ACN (25 mL) and TEA (3.46 mL, 24.85 mmol) and to this solution was added Boc2O (1.50 mL, 6.46 mmol). The reaction was then stirred at rt overnight. The reaction mixture was diluted with EtOAc and washed with water followed by brine. The crude product was then purified using silica gel chromatography to give (R)-tert-butyl(1-(3-chloro-2-fluorophenyl)allyl)carbamate (835 mg, 59%) as a white solid. MS (ESI) m/z: 271.0 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 7.35-7.30 (m, 1H), 7.17 (td, J=7.0, 1.5 Hz, 1H), 7.09-7.03 (m, 1H), 6.03-5.92 (m, 1H), 5.48 (br. s., 1H), 5.26-5.11 (m, 2H), 1.49-1.35 (m, 9H) ppm.

Workup

  1. customhad been consumed
  2. concentrationThe reaction mixture was concentrated
  3. customThe crude product was then triturated with ether
  4. filtrationfiltered
  5. washwashed with ether

Sources & evidence

ORD record
ord-af8494694dbf42288800c044cb9f9538
Source dataset
uspto-grants-2015_08
Patent number
US09108981B2

Reaction notes

Loading…