Hydroxylamine → HCID 58374197, compound

HRID 1948482Notes

Reaction equation

HRID 1948482 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][C@@H:13]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)[CH2:7]1)=[O:5])[CH3:2].[NH2:30][OH:31]>CCO>[Si:23]([O:22][C@@H:13]([C:14]1[CH:15]=[CH:16][C:17](/[C:20](=[N:30]/[OH:31])/[NH2:21])=[CH:18][CH:19]=1)[CH2:12][N:8]1[CH2:9][CH2:10][CH2:11][C@H:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7]1)([C:26]([CH3:28])([CH3:27])[CH3:29])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 58374102HCID 58374102, compound

Product 1

HCID 58374197HCID 58374197, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-Ethyl-1-((S)-2-(tert-butyldimethylsilyloxy)-2-(4-cyanophenyl)ethyl)piperidine-3-carboxylate (31.0 g, 74.4 mmol) was dissolved in EtOH (248 mL). Hydroxylamine (50% aq) (6.84 ml, 112 mmol) was added and stirred at room temperature overnight. Then all volatiles were removed with ROTAVAPOR®. The residue was purified with on a silica gel cartridge (330 g silica, 0-50% EtOAc/hexanes gradient) to give (S)-ethyl 1-((S)-2-(tert-butyldimethylsilyloxy)-2-(4-((Z)-N′-hydroxycarbamimidoyl)phenyl)ethyl)piperidine-3-carboxylate (31 g, 68.9 mmol, 93% yield) as a white foam. 1H NMR (400 MHz, CDCl3) δ ppm 8.38 (1H, br s), 7.58 (2H, d), 7.37 (2H, d), 4.88 (2H, br s), 4.81 (1H, m), 4.13 (2H, m), 2.96 (1H, m), 2.82 (1H, m), 2.61 (1H, dd), 2.51 (1H, m), 2.42 (1H, dd), 2.32 (1H, tt), 2.13 (1H, dt), 1.91 (1H, m), 1.66 (1H, dt), 1.58 (1H, m), 1.48 (1H, m), 1.27 (3H, t), 0.89 (9H, s), 0.08 (3H, s), −0.09 (3H, s).

Workup

  1. customThen all volatiles were removed with ROTAVAPOR®
  2. customThe residue was purified with on a silica gel cartridge (330 g silica, 0-50% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-17863ddfe9d64cd693f9bd8a7132455e
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

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