Diisopropylethylamine → HCID 86660285, compound

HRID 1631045Notes

Reaction equation

HRID 1631045 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:13][N:12]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]#[N:22])=[CH:16][N:15]=2)[C@H:11]([C:23]([O:25][CH3:26])=[O:24])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl.[NH2:28][OH:29].CCN(C(C)C)C(C)C>CCO.C(Cl)Cl>[Si:1]([O:8][C@H:9]1[CH2:13][N:12]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21](=[N:28][OH:29])[NH2:22])=[CH:16][N:15]=2)[C@H:11]([C:23]([O:25][CH3:26])=[O:24])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 86660283HCID 86660283, compound

Product 1

HCID 86660285HCID 86660285, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 21584144Dichloromethane ethanolSolvent

Procedure

A solution of methyl (2S,4R)-4-(tert-butyldimethylsilyloxy)-1-(3-chloro-5-cyanopyridin-2-yl)pyrrolidine-2-carboxylate (0.306 g; 0.77 mmol), hydroxylamine hydrochloride (0.064 g; 0.92 mmol) and DIEA (0.176 mL; 1.01 mmol) in EtOH/DCM (4 mL/2 mL) was stirred at ambient temperature for 96 hours. The solvent was evaporated in vacuo and the residue dissolved in DCM/water. The mixture was passed through a hydrophobic frit and the solvent evaporated in vacuo to afford the title product (0.335 g, 100%). 1H NMR (CDCl3, 400 MHz) δ 8.22 (1H, d, J=2 Hz), 7.76 (1H, d, J=1.6 Hz), 6.60 (1H, br s), 4.87-4.83 (1H, m), 4.73 (2H, br s), 4.54-4.53 (1H, m), 4.26-4.22 (1H, m), 3.75-3.67 (4H, m), 2.26-2.20 (1H, m), 2.09-2.02 (1H, m), 0.85 (9H, s), 0.05-0.08 (6H, m).

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue dissolved in DCM/water
  3. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-6f123790efd34d64910bb62865f79aa7
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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