Triethylsilane → (3R,5S)-5-benzylsulfanylmethyl-1-methanesulfonyl-pyrrolidine-3-thiol

HRID 458318Notes

Reaction equation

HRID 458318 reaction equation
C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C.[CH2:15]([S:22][CH2:23][C@@H:24]1[CH2:28][C@@H:27]([S:29]CC2C=CC(OC)=CC=2)[CH2:26][N:25]1[S:39]([CH3:42])(=[O:41])=[O:40])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[CH2:15]([S:22][CH2:23][C@H:24]1[N:25]([S:39]([CH3:42])(=[O:41])=[O:40])[CH2:26][C@H:27]([SH:29])[CH2:28]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 69430272(2S,4R)-2-benzylsulfanylmethyl-1-methanesulfonyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidineHCID 131722655TFA triethylsilane

Product 1

HCID 86584837(3R,5S)-5-benzylsulfanylmethyl-1-methanesulfonyl-pyrrolidine-3-thiolYield 21%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
80 °C

Procedure

(TFA/triethylsilane for not labile methoxy-benzylsulfanyl, Method 2): 100 mg (0.23 mmol) of (2S,4R)-2-benzylsulfanylmethyl-1-methanesulfonyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidine was dissolved in 8.2 ml TFA and treated at 0° C. with 0.35 ml (2.38 mmol) triethylsilane. The reaction was warmed up over night, heated 2.5 min at 80° C. and evaporated. Flash silica gel column (CH2Cl2/EtOAc 99:1) gave 15 mg (21%)of (3R,5S)-5-benzylsulfanylmethyl-1-methanesulfonyl-pyrrolidine-3-thiol, mp 101.5–103.5° C., MS: 318 (MH+).

Workup

  1. temperatureThe reaction was warmed up over night
  2. customevaporated

Sources & evidence

ORD record
ord-5790dbdecf77469883488df90865198b
Source dataset
uspto-grants-2007_03
Patent number
US07189756B2

Reaction notes

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