Hydrochloric Acid → 2,2,2-Trifluoro-1-(cis-6-hydroxy-2,3,4,4a,9,9a-hexahydro-indeno[2,1-b]pyridin-1-yl)-ethanone

HRID 2272014Notes

Reaction equation

HRID 2272014 reaction equation
B(Br)(Br)Br.[F:5][C:6]([F:25])([F:24])[C:7]([N:9]1[CH2:14][CH2:13][CH2:12][C@@H:11]2[C:15]3[CH:16]=[C:17]([O:22]C)[CH:18]=[CH:19][C:20]=3[CH2:21][C@H:10]12)=[O:8].C([O-])([O-])=O.[K+].[K+].Cl>ClCCl>[F:25][C:6]([F:5])([F:24])[C:7]([N:9]1[CH2:14][CH2:13][CH2:12][C@@H:11]2[C:15]3[CH:16]=[C:17]([OH:22])[CH:18]=[CH:19][C:20]=3[CH2:21][C@H:10]12)=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 25134Boron tribromideHCID 582946492,2,2-Trifluoro-1-(cis-6-methoxy-2,3,4,4a,9,9a-hexahydro-indeno[2,1-b]pyridin-1-yl)-ethanone

Product 1

HCID 582944732,2,2-Trifluoro-1-(cis-6-hydroxy-2,3,4,4a,9,9a-hexahydro-indeno[2,1-b]pyridin-1-yl)-ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Boron tribromide (1 mol/L in heptane, 27 mL) is added to a solution of 2,2,2-trifluoro-1-(cis-6-methoxy-2,3,4,4a,9,9a-hexahydro-indeno[2,1-b]pyridin-1-yl)-ethanone (8.1 g) in dichloromethane (120 mL) chilled in an ice bath. The resulting mixture is warmed in the cooling bath to room temperature overnight. The solution is cooled again in an ice bath, diluted with dichloromethane (50 mL), and then 25% aqueous K2CO3 (20 mL) is carefully added. The mixture is stirred for 30 min and then acidified by the addition of 4 M aqueous hydrochloric acid (60 mL). The organic phase is separated, washed with 1 M aqueous hydrochloric acid (40 mL), and dried (MgSO4). The solvent is evaporated to give the title compound as a solid. Yield: 7.3 g (95% of theory); LC (method 1): tR=3.43 min; Mass spectrum (ESI+): m/z=286 [M+H]+.

Workup

  1. temperaturechilled in an ice bath
  2. temperatureThe solution is cooled again in an ice bath
  3. customThe organic phase is separated
  4. washwashed with 1 M aqueous hydrochloric acid (40 mL)
  5. dry with materialdried (MgSO4)
  6. customThe solvent is evaporated

Sources & evidence

ORD record
ord-299e76e37d9c4e499e13dae3415438b4
Source dataset
uspto-grants-2015_09
Patent number
US09120769B2

Reaction notes

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