Propargyl bromide → HCID 86692134, compound

HRID 527895Notes

Reaction equation

HRID 527895 reaction equation
[CH:1]1([NH:6][C@@H:7]2[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:20][C:21]#[CH:22].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH:1]1([N:6]([CH2:22][C:21]#[CH:20])[C@@H:7]2[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 68027349HCID 68027349, compound

Product 1

HCID 86692134HCID 86692134, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (R)-tert-butyl 3-(cyclopentylamino)pyrrolidine-1-carboxylate (200 mg, 0.78 mmol), 3-bromo-1-propyne (140 mg, 1.18 mmol) and K2CO3 (217 mg, 1.57 mmol) in acetonitrile (3 mL) was stirred at reflux for overnight. The volatiles were removed under reduced pressure. The residue was purified by chromatography on silica gel (PE/EtOAc=4:1) to give the title compound. MS (m/z): 293 (M+H)+.

Workup

  1. temperatureat reflux for overnight
  2. customThe volatiles were removed under reduced pressure
  3. customThe residue was purified by chromatography on silica gel (PE/EtOAc=4:1)

Sources & evidence

ORD record
ord-753703df54da4cc09bec3dda13c7043c
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

Loading…