Triethylsilane → HCID 22671649, compound

HRID 1006856Notes

Reaction equation

HRID 1006856 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[CH:15]([S:16]CC2C=CC(OC)=CC=2)[CH2:14][CH2:13][N:12]([S:26]([C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=2)(=[O:28])=[O:27])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[CH2:1]([O:8][CH2:9][CH:10]1[CH:15]([SH:16])[CH2:14][CH2:13][N:12]([S:26]([C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=2)(=[O:28])=[O:27])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 22671587HCID 22671587, compound

Product 1

HCID 22671649HCID 22671649, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

84 mg (0.153 mmol) (3SR,4RS)-3-Benzyloxymethyl-4-(4-methoxy-benzylsulfanyl)-1-(naphthalene-2-sulfonyl)-piperidine were dissolved in 2 ml TFA and treated at 0° C. with 0.244 ml (1.53 mmol) of triethylsilane. After 2 h at 0° C. and 18 h at room temperature, the mixture was evaporated and purified by precipitation with Et2O/pentane to give 40 mg (61%) of (3SR,4RS)-3-benzyloxymethyl-1-(naphthalene-2-sulfonyl)-piperidine-4-thiol, MS: 427 (M).

Workup

  1. custom18 h at room temperature, the mixture was evaporated
  2. custompurified by precipitation with Et2O/pentane

Sources & evidence

ORD record
ord-97debc48672c42d0a284591306ffcabb
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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