(Diethylamino)sulfur trifluoride → HCID 53985269, compound

HRID 1005006Notes

Reaction equation

HRID 1005006 reaction equation
C(N(S(F)(F)[F:7])CC)C.[CH2:10]([O:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[C:20]([CH2:28][O:29][CH:30]2[CH:35]([C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([CH2:42]O)[CH:37]=3)[CH2:34][CH2:33][N:32]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:31]2)[CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl>[CH2:10]([O:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[C:20]([CH2:28][O:29][CH:30]2[CH:35]([C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([CH2:42][F:7])[CH:37]=3)[CH2:34][CH2:33][N:32]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:31]2)[CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 54536116tert-butyl (3RS,4RS)-3-(4-benzyloxy-naphthalen-2-ylmethoxy)-4-(3-hydroxymethyl-phenyl)-piperidine-1-carboxylate

Product 1

HCID 53985269HCID 53985269, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 18 mg (0.106 mmol) of diethylamino-sulphur trifluoride (DAST) in 1 ml of methylene chloride was cooled to -65° C. and a solution of 56 mg (0.101 mmol) of tert-butyl (3RS,4RS)-3-(4-benzyloxy-naphthalen-2-ylmethoxy)-4-(3-hydroxymethyl-phenyl)-piperidine-1-carboxylate in 1 ml of methylene chloride was added dropwise thereto at -60° C. to -65° C. within 3 minutes. The resulting yellow solution was warmed to room temperature and stirred for one hour. Subsequently, the mixture was partitioned between methylene chloride and 5% sodium hydrogen carbonate solution, the organic phase was dried over magnesium sulphate and finally the solvent was distilled off under reduced pressure. There were obtained 57 mg of crude tert-butyl (3RS,4RS)-3-(4-benzyloxy-naphthalen-2-ylmethoxy)-4-(3-fluoromethyl-phenyl)-piperidine-1-carboxylate, which was used in the next step without further purification and characterization.

Workup

  1. customSubsequently, the mixture was partitioned between methylene chloride and 5% sodium hydrogen carbonate solution
  2. dry with materialthe organic phase was dried over magnesium sulphate
  3. distillationfinally the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e1c20ddf1e87465b8aa418e8b9b8386c
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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