Boron tribromide → (1R*,2R*)-1,2,3,4-tetrahydro-6-hydroxy-2-(4-hydroxyphenyl)-1-(1H-imidazol-1-ylmethyl)naphthalene

HRID 1165513Notes

Reaction equation

HRID 1165513 reaction equation
[N:1]1([CH2:6][C@H:7]2[C:16]3[C:11](=[CH:12][C:13]([O:17]C)=[CH:14][CH:15]=3)[CH2:10][CH2:9][C@H:8]2[C:19]2[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.B(Br)(Br)Br.[Na]>ClCCl>[OH:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[C@H:7]([CH2:6][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)[C@H:8]([C:19]1[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=1)[CH2:9][CH2:10]2

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 5360545SodiumHCID 53804055(1R*,2R*)-1,2,3,4-tetrahydro-1-(1H-imidazol-1-ylmethyl)-6-methoxy-2-(4-methoxyphenyl)naphthalene

Product 1

HCID 54394449(1R*,2R*)-1,2,3,4-tetrahydro-6-hydroxy-2-(4-hydroxyphenyl)-1-(1H-imidazol-1-ylmethyl)naphthalene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (1R*,2R*)-1,2,3,4-tetrahydro-1-(1H-imidazol-1-ylmethyl)-6-methoxy-2-(4-methoxyphenyl)naphthalene, (prepared as described in Example 1), in dichloromethane (20 ml) was stirred in an argon atmosphere and cooled in an acetone/solid carbon dioxide bath while a 1M solution of boron tribromide was added dropwise over 5 minutes. The mixture was kept at -20° for 48 h, then poured into a mixture of saturated sodium bicaronate solution (30 ml) and stirred vigorously for 2 h. The solid thus obtained was filtered off, washed with water (100 ml) then dichloromethane (100 ml) and dried in a desiccator under reduced pressure to give (1R*,2R*)-1,2,3,4-tetrahydro-6-hydroxy-2-(4-hydroxyphenyl)-1-(1H-imidazol-1-ylmethyl)naphthalene, m.p. 238°.

Workup

  1. additionwas added dropwise over 5 minutes
  2. customThe solid thus obtained
  3. filtrationwas filtered off
  4. washwashed with water (100 ml)
  5. dry with materialdichloromethane (100 ml) and dried in a desiccator under reduced pressure

Sources & evidence

ORD record
ord-8134b109d59f4156bb63bae66143e7a0
Source dataset
uspto-grants-1990_03
Patent number
US04910212

Reaction notes

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