Triethylamine → HCID 86708280, compound

HRID 534240Notes

Reaction equation

HRID 534240 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]([N:5]([C@@H:12]1[CH2:14][C@H:13]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:6][C@H:7]1[CH2:11][CH2:10][NH:9][CH2:8]1)=[O:4].[C:23]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])(=[O:26])[CH:24]=[CH2:25].C(N(CC)CC)C>O1CCCC1>[F:22][C:2]([F:1])([F:21])[C:3]([N:5]([CH2:6][C@H:7]1[CH2:11][CH2:10][N:9]([CH2:25][CH2:24][C:23]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:8]1)[C@@H:12]1[CH2:14][C@H:13]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15458tert-Butyl acrylateHCID 86708278HCID 86708278, compound

Product 1

HCID 86708280HCID 86708280, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,2,2-trifluoro-N-((1R,2S)-2-phenylcyclopropyl)-N-((S)-pyrrolidin-3-ylmethyl)acetamide (140 mg, 0.448 mmol) in tetrahydrofuran (3 mL) were added tert-butyl acrylate (0.085 mL, 0.583 mmol) and triethylamine (0.094 mL, 0.672 mmol), and the mixture was stirred at room temperature for 20 h. The mixture was concentrated and the residue was purified using column chromatography (silica gel, 0 to 100% EtOAc/hexanes) to give 110 mg of product as pale yellow oil.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified

Sources & evidence

ORD record
ord-6bd96df183d24f58ac16adba6fe9e0a7
Source dataset
uspto-grants-2014_10
Patent number
US08853408B2

Reaction notes

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