5-Chlorothiophene-2-carbonyl Chloride → tert. Butyl 3-[(5-chloro-thiophene-2-carbonyl)-amino]-pyrrolidine-1-carboxylate

HRID 1875324Notes

Reaction equation

HRID 1875324 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.[Cl:14][C:15]1[S:19][C:18]([C:20](Cl)=[O:21])=[CH:17][CH:16]=1>C(Cl)Cl>[Cl:14][C:15]1[S:19][C:18]([C:20]([NH:1][CH:2]2[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]2)=[O:21])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 5892235-Chlorothiophene-2-carbonyl ChlorideHCID 27563701-Boc-3-aminopyrrolidine

Product 1

HCID 68646970tert. Butyl 3-[(5-chloro-thiophene-2-carbonyl)-amino]-pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.5 g (2.7 mmol) tert. Butyl 3-amino-pyrrolidine-1-carboxylate are dissolved in 7 ml DCM, combined with 1.4 ml (10.1 mmol) TEA and 0.5 g (2.7 mmol) 5-chloro-thiophene-2-carboxylic acid chloride and stirred for one hour at RT. The reaction mixture is diluted with DCM and washed successively with dil. aqueous KHSO4 solution, sat. aqueous NaHCO3 solution and water. The combined organic phases are dried on sodium sulphate and evaporated to dryness i. vac.

Workup

  1. washwashed successively with dil. aqueous KHSO4 solution, sat. aqueous NaHCO3 solution and water
  2. customThe combined organic phases are dried on sodium sulphate
  3. customevaporated to dryness i

Sources & evidence

ORD record
ord-c32fbf20bda846a49cf2ae3ac3baa02f
Source dataset
uspto-grants-2012_11
Patent number
US08309542B2

Reaction notes

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