Pyrrolidine → HCID 42643387, compound

HRID 1162627Notes

Reaction equation

HRID 1162627 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([NH:13][C:14]([C:16]2[S:17][C:18]([Cl:21])=[CH:19][CH:20]=2)=[O:15])[CH2:10][C@H:9]1[CH2:22]OS(C)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([NH:13][C:14]([C:16]2[S:17][C:18]([Cl:21])=[CH:19][CH:20]=2)=[O:15])[CH2:10][C@H:9]1[CH2:22][N:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 42643385HCID 42643385, compound

Product 1

HCID 42643387HCID 42643387, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

17.3 To a stirred solution of 200 mg (2S,4R)-4-[(5-chloro-thiophene-2-carbonyl)-amino]-2-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester at r.t. in 5 ml THF under an argon atmosphere were added 0.38 ml pyrrolidine. The mixture was heated to reflux for 6 h, then cooled to r.t. and concentrated. The crude product was purified by column chromatography (silica gel, gradient CH2Cl2->CH2Cl2/MeOH 9:1) to give 138 mg (2S,4R)-4-[(5-chloro-thiophene-2-carbonyl)-amino]-2-pyrrolidin-1-ylmethyl-pyrrolidine-1-carboxylic acid tert-butyl ester as off-white amorphous solid. MS 414.4 ([M+H]+)

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 6 h
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography (silica gel, gradient CH2Cl2->CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-40f24d48040f4ebbbae8c51a2e8e7561
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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