Boron tribromide → HCID 14620599, compound

HRID 231824Notes

Reaction equation

HRID 231824 reaction equation
C[O:2][C:3]1[CH:24]=[CH:23][C:22]2[CH:9]3[CH2:10][C:11]4[CH:18]=[C:17]5[O:19]C[O:21][C:16]5=[CH:15][C:12]=4[CH2:13][CH2:14][N:8]3[CH2:7][CH2:6][C:5]=2[CH:4]=1.B(Br)(Br)Br>C(O)C.Cl>[CH:23]1[C:22]2[CH:9]3[CH2:10][C:11]4[CH:18]=[C:17]([OH:19])[C:16]([OH:21])=[CH:15][C:12]=4[CH2:13][CH2:14][N:8]3[CH2:7][CH2:6][C:5]=2[CH:4]=[C:3]([OH:2])[CH:24]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 14620592HCID 14620592, compound

Product 1

HCID 14620599HCID 14620599, compoundYield 108.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent2×

Procedure

The title compound was prepared as described in Example 22 by the treatment of 5,6,8,9,15,15a-hexahydro-3-methoxy-[1,3]dioxolo[4,5-h]isoquino[1,2-b][3]benzazepine (XIIIb, Ex. 19) (0.9 g, 2.8 mmole) with boron tribromide. The reaction time was shortened to 4 hours. Evaporation of ethyl acetate extracts on a rotary evaporator afforded a solid residue which was dissolved in hot ethanol solution with ethanolic hydrogen chloride solution. When the mixture was warmed on a steam bath with an additional amount of ethanol (15 ml), a crystalline product was separated. The mixture was chilled in a refrigerator, and the precipitate was collected on a filter and washed with ethanol to give the titled product (0.9 g, 97%). An analytical sample was obtained by dissolving the product in a mixture of ethanol and a small amount of water, and precipitation by an addition of a large amount of anhydrous ether. The product started to char at 282° and decomposed completely at 286°. Mass spec (CI) m/z 298 (M+1) and 247.

Workup

  1. customThe title compound was prepared
  2. customEvaporation of ethyl acetate extracts
  3. customon a rotary evaporator
  4. customafforded a solid residue which
  5. customa crystalline product was separated
  6. temperatureThe mixture was chilled in a refrigerator
  7. customthe precipitate was collected on
  8. filtrationa filter
  9. washwashed with ethanol

Sources & evidence

ORD record
ord-a6a585f4a85441e2b2062be526158405
Source dataset
uspto-grants-1989_07
Patent number
US04849420

Reaction notes

Loading…