3-Bromo-1-propanol → HCID 178484808, compound

HRID 25568

Reaction equation

HRID 25568 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][OH:5].C(C1C=CC=C(C(C)(C)C)N=1)(C)(C)C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.O[CH2:36][C@H:37]1[CH2:42][CH2:41][C@H:40]([N:43]([CH3:57])[S:44]([C:47]2[CH:52]=[CH:51][C:50]([C:53]([F:56])([F:55])[F:54])=[CH:49][CH:48]=2)(=[O:46])=[O:45])[CH2:39][CH2:38]1>C(Cl)Cl.[N+](C)([O-])=O>[Br:1][CH2:2][CH2:3][CH2:4][O:5][CH2:36][C@H:37]1[CH2:38][CH2:39][C@H:40]([N:43]([CH3:57])[S:44]([C:47]2[CH:48]=[CH:49][C:50]([C:53]([F:56])([F:54])[F:55])=[CH:51][CH:52]=2)(=[O:45])=[O:46])[CH2:41][CH2:42]1

Participants

7

Reactant 4

HCID 123083-Bromo-1-propanolHCID 67749Trifluoromethanesulfonic anhydrideHCID 685102,6-Di-tert-butylpyridine2×HCID 178484807HCID 178484807, compound

Product 1

HCID 178484808HCID 178484808, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6375NitromethaneSolvent

Conditions

Temperature
60 °C

Procedure

[following a procedure of Belostotskii, Anatoly M.; Hassner, Alfred. Synthetic methods. 41. Etherification of hydroxysteroids via triflates. Tetrahedron Lett. (1994), 35(28), 5075-6.]. A solution of 0.175 ml (2 mmol) 3-bromo-1-propanol and 0.48 ml 2,6-di-tert-butylpyridine in 1 ml CH2Cl2 was treated at 0° C. with a solution of 0.35 ml (2.1 mmol) trifluoromethansulfonic anhydride in 0.5 ml CH2Cl2. After 2.5 h at 0° C., the violet solution was evaporated, dissolved in 1 ml nitromethane and treated with a solution of 0.375 g (1 mmol) trans-N-(4-Hydroxymethyl-cyclohexyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide and 0.45 ml (2 mmol) 2,6-di-tert-butylpyridine in 3 ml nitromethane (during 3 min). The reaction was heated (60° C.) for 3.5 h and then extracted with aqueous 10% KHSO4/EtOAc (3×). The organic phases were washed with aqueous saturated NaHCO3, aqueous 10% NaCl, dried over Na2SO4 and evaporated. Purification by flash-chromatography on silica gel (hexane/EtOAc 9:1) yielded 0.3 g (64%) of trans-N-[4-(3-Bromo-propoxymethyl)-cyclohexyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide, MS: 452 (M−F, 1Br).

Workup

  1. customthe violet solution was evaporated
  2. dissolutiondissolved in 1 ml nitromethane
  3. extractionextracted with aqueous 10% KHSO4/EtOAc (3×)
  4. washThe organic phases were washed with aqueous saturated NaHCO3, aqueous 10% NaCl
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customPurification by flash-chromatography on silica gel (hexane/EtOAc 9:1)

Sources & evidence

ORD record
ord-e6ad2b77c6dc4d59a3205a97d0fa2108
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Linked notes

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