Triethylamine → HCID 67218707, compound

HRID 900886Notes

Reaction equation

HRID 900886 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1.[Cl:7][C:8]1[S:12][C:11]([S:13](Cl)(=[O:15])=[O:14])=[CH:10][C:9]=1[N+:17]([O-:19])=[O:18].C(N(CC)CC)C>C1COCC1>[Cl:7][C:8]1[S:12][C:11]([S:13]([N:1]2[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]2)(=[O:14])=[O:15])=[CH:10][C:9]=1[N+:17]([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 982104-HydroxypyrrolidineHCID 27357835-Chloro-4-nitrothiophene-2-sulfonyl chloride

Product 1

HCID 67218707HCID 67218707, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (RS)-3-pyrrolidinol (0.75 g, 8.6 mmol) in THF (18 ml) was added at room temperature 5-chloro-4-nitrothiophene-2-sulfonyl chloride (1.5 g, 5.72 mmol) and triethylamine (0.88 ml, 6.3 mmol). The light yellow suspension was stirred at room temperature for 17 h, and evaporated. The crude product was further purified by column chromatography on silica gel (ethyl acetate), and subsequent crystallization from dichloromethane/MeOH/hexane to yield (RS)-1-(5-chloro-4-nitro-thiophene-2-sulfonyl)-pyrrolidin-3-ol (0.65 g, 36%) as a yellow solid. MS (EI) 312.0 [(M)+], mp 96° C.

Workup

  1. customevaporated
  2. customThe crude product was further purified by column chromatography on silica gel (ethyl acetate), and subsequent crystallization from dichloromethane/MeOH/hexane

Sources & evidence

ORD record
ord-b53eaa4bacb745aeb72c1ef7fca9625b
Source dataset
uspto-grants-2008_04
Patent number
US07361659B2

Reaction notes

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