Triethylamine → HCID 57477135, compound

HRID 527383Notes

Reaction equation

HRID 527383 reaction equation
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[NH2:11][C@H:12]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13]1.C(N(CC)CC)C>C(Cl)Cl>[N:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([NH:11][C@H:12]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13]2)=[O:9])[CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylate

Product 1

HCID 57477135HCID 57477135, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Nicotinoyl chloride hydrochloride (286 mg, 1.61 mmol, 1.0 eq) was added at room temperature to a stirred solution of (S)-3-amino-1-N-BOC-pyrrolidine (300 mg, 1.61 mmol, 1.0 eq) in CH2Cl2 (9 mL), followed by triethylamine (337 μL, 2.42 mmol, 1.5 eq). After stirring overnight at room temperature, the reaction mixture was extracted and the organic layer was dried over Na2SO4, filtered and evaporated to afford 457 mg of the expected compound.

Workup

  1. extractionthe reaction mixture was extracted
  2. dry with materialthe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-76ff9dd432054f958b8127280f97d0de
Source dataset
uspto-grants-2016_05
Patent number
US09346799B2

Reaction notes

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