Methanol → HCID 70374341, compound

HRID 1032271Notes

Reaction equation

HRID 1032271 reaction equation
[CH3:1][CH:2]1[CH2:12][CH:11]2[CH2:13][CH2:14][CH2:15][C:9]3=[C:10]2[CH:4]([CH2:5][N:6]([O:16]C)[CH:7]=[CH:8]3)[CH2:3]1.B(Br)(Br)Br.CO>ClCCl>[CH3:1][CH:2]1[CH2:12][CH:11]2[CH2:13][CH2:14][CH2:15][C:9]3=[C:10]2[CH:4]([CH2:5][N:6]([OH:16])[CH:7]=[CH:8]3)[CH2:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 70374203HCID 70374203, compound

Product 1

HCID 70374341HCID 70374341, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2.31 g (10 mmol) of 2-methyl-5-methoxy-1,2,3,4,8,9,10,10a-octahydronaphth[1,8-cd]azepine in 25 ml of dichloromethane was cooled to -70° C., and 20 ml of 1M boron tribromide in dichloromethane was added. The mixture was allowed to warm to room temperature and then cooled to -40° C., and then treated with 10 ml of methanol. Solvents were removed under reduced pressure and the residue was crystallized from methanol ether to afford 1.8 g (60%) of 2-methyl-5-hydroxy-1,2,3,4,8,9,10,10a-octahydronaphth[1,8-cd]azepine (HBr salt, mp 217°-218° C.).

Workup

  1. temperaturecooled to -40° C.
  2. customSolvents were removed under reduced pressure
  3. customthe residue was crystallized from methanol ether

Sources & evidence

ORD record
ord-02b7e98cbd2044ec86ddfa82e21d88a7
Source dataset
uspto-grants-1990_09
Patent number
US04957914

Reaction notes

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