Triethylamine → HCID 57731993, compound

HRID 401796Notes

Reaction equation

HRID 401796 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[F:6][C:7]1[CH:12]=[CH:11][C:10]([C@H:13]2[CH2:17][O:16][CH2:15][C@H:14]2[OH:18])=[CH:9][CH:8]=1.CCN(CC)CC>C(Cl)Cl.O>[CH3:4][S:1]([O:18][C@@H:14]1[C@@H:13]([C:10]2[CH:11]=[CH:12][C:7]([F:6])=[CH:8][CH:9]=2)[CH2:17][O:16][CH2:15]1)(=[O:3])=[O:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68536137HCID 68536137, compound

Product 1

HCID 57731993HCID 57731993, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Mesyl chloride (21.4 mL, 0.28 mol, 1.2 eq) was added dropwise to a mixture of compound (3S*,4S*)-4-(4-fluorophenyl)tetrahydrofuran-3-ol (Preparation 59, 42 g, 0.23 mol, 1 eq) and Et3N (79.6 mL, 0.55 mol, 2.0 eq) in DCM (250 mL) under stirring on an ice bath for 30 min. The mixture was stirred at room temperature for 1 h and diluted with water (500 mL). The layers were separated. The organic layer was subjected to chromatography on silica (1 L, carbon tetrachloride→25, 50, 75, 100% chloroform→MeOH) to give title compound (40 g, 0.15 mol, 67%).

Workup

  1. stirringThe mixture was stirred at room temperature for 1 h
  2. customThe layers were separated

Sources & evidence

ORD record
ord-4617c1b1a443478aa70b5aa49e367706
Source dataset
uspto-grants-2014_06
Patent number
US08741934B2

Reaction notes

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