tert-Octylamine → HCID 10379427, compound

HRID 475384Notes

Reaction equation

HRID 475384 reaction equation
Cl[CH2:2][C:3]([N:5]1[C@@H:9]([C:10]#[CH:11])[CH2:8][CH2:7][C@H:6]1[C:12]#[N:13])=[O:4].[CH3:14][C:15]([NH2:22])([CH3:21])[CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18]>C(#N)C>[C:10]([C@@H:9]1[N:5]([C:3](=[O:4])[CH2:2][NH:22][C:15]([CH3:21])([CH3:14])[CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C@H:6]([C:12]#[N:13])[CH2:7][CH2:8]1)#[CH:11]

Participants

4

Reactant 2

HCID 61017tert-OctylamineHCID 16090854(2S,5R)-1-(2-chloroacetyl)-5-ethynylpyrrolidine-2-carbonitrile

Product 1

HCID 10379427HCID 10379427, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of (2S,5R)-1-(chloroacetyl)-5-ethynylpyrrolidine-2-carbonitrile (0.04 g, 0.20 mmol, Example 8D) in acetonitrile (3 mL) at room temperature under nitrogen was added 1,1,3,3-tetramethylbutylamine (0.066 g, 0.406 mmol). The reaction mixture was stirred for two days and then concentrated under reduced pressure. The residue was flash chromatographed with 2% MeOH/CH2Cl2 to provide the titled compound. MS (DCI) m/z 290 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 1.5-2.02 (10H, m), 2.07-2.21 (2H, m), 2.45-2.50 (2H, m), 3.03-3.5 (6 Hs), 3.76 (1H, d), 3.78-4.53 (2H, m), 4.53-4.55 (1H, t), 5.06 (1H, m), 5.1 (1H, m).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customchromatographed with 2% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-2bee24f69a134e1fb5d415c2971f215b
Source dataset
uspto-grants-2014_01
Patent number
US08637546B2

Reaction notes

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