Triethylsilane → HCID 86584847, compound

HRID 1006809Notes

Reaction equation

HRID 1006809 reaction equation
[CH3:1][S:2]([N:5]1[CH2:9][C@H:8]([S:10]CC2C=CC(OC)=CC=2)[CH2:7][C@H:6]1[CH2:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:4])=[O:3].C([SiH](CC)CC)C>>[CH3:1][S:2]([N:5]1[C@H:6]([CH2:20][O:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:7][C@@H:8]([SH:10])[CH2:9]1)(=[O:3])=[O:4]

Participants

3

Reactant 2

HCID 12052TriethylsilaneHCID 18440955HCID 18440955, compound

Product 1

HCID 86584847HCID 86584847, compoundYield 54.3%

Procedure

(Method 2): A solution of 102 mg (0.25 mmol) (2S,4R)-1-methanesulfonyl-4-(4-methoxy-benzylsulfanyl)-2-phenoxymethyl-pyrrolidine and 0.4 ml (2.5 mmol) triethylsilane was heated for 1 min at 80° C., cooled to room temperature and evaporated. Crystallization from Et2O/pentane gave 39 mg (54%) of (3R,5S)-1-methanesulfonyl-5-phenoxymethyl-pyrrolidine-3-thiol, mp 78-79° C., MS: 288 (MH+).

Workup

  1. customevaporated
  2. customCrystallization from Et2O/pentane

Sources & evidence

ORD record
ord-1567d030e7614c8a9741713139f408f5
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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