Boron tribromide → N-benzyl-(1-hydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine

HRID 1936968Notes

Reaction equation

HRID 1936968 reaction equation
[CH2:1]([NH:8][CH:9]1[CH2:15][CH2:14][CH2:13][C:12]2[C:16]([O:20]C)=[CH:17][CH:18]=[CH:19][C:11]=2[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>ClCCl>[CH2:1]([NH:8][CH:9]1[CH2:15][CH2:14][CH2:13][C:12]2[C:16]([OH:20])=[CH:17][CH:18]=[CH:19][C:11]=2[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 18007167N-benzyl-(1-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine

Product 1

HCID 22462907N-benzyl-(1-hydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amineYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under nitrogen, N-benzyl-(1-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine (4.5 g) in dichloromethane (45 ml) was added boron tribromide (1M in dichloromethane, 32 ml) dropwise at 0° C., and the mixture was stirred at the same temperature for 2 hours. The resulting mixture was poured into ice-cold water and the precipitate was collected by filtration. The filter cake was added to the mixture of water and ethyl acetate, and then adjusted to pH 9 with 1N sodium hydroxide. After separation, the organic layer was dried over anhydrous magnesium sulfate and evaporated in vacuo to afford N-benzyl-(1-hydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine (3.72 g).

Workup

  1. additionThe resulting mixture was poured into ice-cold water
  2. filtrationthe precipitate was collected by filtration
  3. additionThe filter cake was added to the mixture of water and ethyl acetate
  4. customAfter separation
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-f9fbfe092df349de921f111eeecd9eea
Source dataset
uspto-grants-2002_05
Patent number
US06391915B2

Reaction notes

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