Methanol → 2-(3,5-Dimethylisoxazole-4-sulfonyl)-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinolin-6-ol

HRID 397087Notes

Reaction equation

HRID 397087 reaction equation
B(Br)(Br)Br.C([O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)=[CH:25][CH:24]=1)[N:18]([S:37]([C:40]1[C:41]([CH3:46])=[N:42][O:43][C:44]=1[CH3:45])(=[O:39])=[O:38])[CH2:17][CH2:16]2)C1C=CC=CC=1.CO>C(Cl)Cl>[CH3:46][C:41]1[C:40]([S:37]([N:18]2[CH2:17][CH2:16][C:15]3[C:20](=[CH:21][CH:22]=[C:13]([OH:12])[CH:14]=3)[CH:19]2[C:23]2[CH:24]=[CH:25][C:26]([O:29][CH2:30][CH2:31][N:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)=[CH:27][CH:28]=2)(=[O:39])=[O:38])=[C:44]([CH3:45])[O:43][N:42]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 18172419HCID 18172419, compound

Product 1

HCID 181724312-(3,5-Dimethylisoxazole-4-sulfonyl)-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinolin-6-olYield 35.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A 1M solution of BBr3 in CH2Cl2 (0.095 ml, 0.095 mmol) was added slowly to a solution of 6-benzyloxy-2-(3,5-dimethylisoxazole-4-sulfonyl)-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline (0.037 g, 0.063 mmol) in anhydrous CH2Cl2 (10 ml) at 0° C. under N2. The reaction mixture was stirred at 0° C. for 1 hr, then warmed to rt and stirred at rt for 4 hr. MeOH (5 ml) was slowly added with stirring and the resulting solution was concentrated in vacuo to an orange residue. Purification by preparative TLC, eluting with EtOAc:MeOH (1:1), and then purification again by preparative TLC, eluting with EtOAc:MeOH (8:2), gave 0.011 g (35% yield) of white solid.

Workup

  1. temperaturewarmed to rt
  2. stirringstirred at rt for 4 hr
  3. stirringwith stirring
  4. concentrationthe resulting solution was concentrated in vacuo to an orange residue
  5. customPurification by preparative TLC
  6. washeluting with EtOAc:MeOH (1:1)
  7. custompurification again by preparative TLC
  8. washeluting with EtOAc:MeOH (8:2)

Sources & evidence

ORD record
ord-50e8f3c99abc460e83558b37a33c2749
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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