Phenol → 4-((2s)-2-Hydroxy-3-{[1-(4-methoxy-benzenesulfonyl)-piperidin-4-ylmethyl]-amino}-propoxy)-phenol

HRID 1634790Notes

Reaction equation

HRID 1634790 reaction equation
C([Si]([O:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C@@H:27]2[CH2:29][O:28]2)=[CH:21][CH:20]=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C.NCC1CCN([C:38]2[CH:43]=[C:42]([O:44][CH3:45])[CH:41]=[CH:40][C:39]=2[S:46]([NH2:49])(=[O:48])=[O:47])CC1.[C:50]1(O)[CH:55]=[CH:54][CH:53]=[CH:52]C=1.CCC[CH2:60][N+:61](CCCC)(CCCC)CCCC.[F-]>CO.C1COCC1>[OH:28][C@@H:27]([CH2:29][NH:61][CH2:60][CH:54]1[CH2:53][CH2:52][N:49]([S:46]([C:39]2[CH:38]=[CH:43][C:42]([O:44][CH3:45])=[CH:41][CH:40]=2)(=[O:47])=[O:48])[CH2:50][CH2:55]1)[CH2:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([OH:18])=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 2724141Tetrabutylammonium FluorideHCID 11327180t-butyl-[4-(2S)-oxiranylmethoxy-phenoxy]-diphenylsilaneHCID 18678703HCID 18678703, compound

Product 1

HCID 102258704-((2s)-2-Hydroxy-3-{[1-(4-methoxy-benzenesulfonyl)-piperidin-4-ylmethyl]-amino}-propoxy)-phenol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of t-butyl-[4-(2S)-oxiranylmethoxy-phenoxy]-diphenylsilane (0.078 g, 0.19 mmol) and an excess of and (4-aminomethyl-1-piperidinyl)-4-methoxybenzene-sulfonamide (0.109 g, 0.38 mmol) was heated as a solution in methanol at 60° C. for 24 hours. The reaction mixture was preabsorbed on silica gel and purified by flash chromatography (CH2Cl2—CH3OH, 19:1) to give the intermediate silyl-protected product. Deprotection to the phenol was accomplished by treatment of the silyl intermediate with 1M TBAF in THF. After stirring 15 minutes the solvent was evaporated and the product isolated by flash chromatography (CH2Cl2—CH3OH, 12:1) to give 0.049 g of the title compound as a white solid.

Workup

  1. customThe reaction mixture was preabsorbed on silica gel
  2. custompurified by flash chromatography (CH2Cl2—CH3OH, 19:1)
  3. customto give the intermediate silyl-
  4. customwas evaporated
  5. customthe product isolated by flash chromatography (CH2Cl2—CH3OH, 12:1)

Sources & evidence

ORD record
ord-b916ab1570e34d02b5f3d20c2f717364
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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