Water → HCID 58375018, compound

HRID 536691Notes

Reaction equation

HRID 536691 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[C:12]2[CH2:13][C@@H:14]3[C:19]([CH3:21])([CH3:20])[C@:18]([CH3:22])([C:11]=2[CH:10]=[CH:9][CH:8]=1)[CH2:17][CH2:16][N:15]3[C:23]([C:25]1[CH:29]=[CH:28][O:27][C:26]=1[CH3:30])=[O:24].O>ClCCl>[OH:6][C:7]1[C:12]2[CH2:13][C@@H:14]3[C:19]([CH3:21])([CH3:20])[C@:18]([CH3:22])([C:11]=2[CH:10]=[CH:9][CH:8]=1)[CH2:17][CH2:16][N:15]3[C:23]([C:25]1[CH:29]=[CH:28][O:27][C:26]=1[CH3:30])=[O:24]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 67345455HCID 67345455, compound

Product 1

HCID 58375018HCID 58375018, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (2 mL) is added to a solution of [(2R,6S)-10-methoxy-6,11,11-trimethyl-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocin-3-yl]-(2-methyl-furan-3-yl)-methanone (0.22 g) in dichloromethane (10 mL). The resulting solution is stirred at ambient temperature for 2 h. Then, water is added and the mixture is stirred for another 10 min. The organic phase is separated and the aqueous phase is extracted with dichloromethane. The combined organic phases are washed with brine and dried (Na2SO4). The solvent is evaporated to give the title compound.

Workup

  1. stirringthe mixture is stirred for another 10 min
  2. customThe organic phase is separated
  3. extractionthe aqueous phase is extracted with dichloromethane
  4. washThe combined organic phases are washed with brine
  5. dry with materialdried (Na2SO4)
  6. customThe solvent is evaporated

Sources & evidence

ORD record
ord-adb29305dffc4633bfc12f233417be0a
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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