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 2360792Notes

Reaction equation

HRID 2360792 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-b5cafcc5842545fa9d4c267c26128dc5
Source dataset
uspto-grants-2014_04
Patent number
US08686149B2

Reaction notes

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