Hydroxylamine → HCID 178472248, compound

HRID 1365728Notes

Reaction equation

HRID 1365728 reaction equation
[CH2:1]1[O:9][C:4]2([CH2:8][CH2:7][CH2:6][CH2:5]2)[O:3][CH2:2]1.C[Si]([C:14]#[N:15])(C)C.[NH2:16][OH:17].[C:18]([C:25]([O:27][CH2:28][CH3:29])=[O:26])#[C:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>O.[Zn+2].[I-].[I-].CCO>[CH2:23]([O:22][C:20](=[O:21])/[C:19](/[O:17][NH:16][C:14]([C:4]1([O:9][CH2:1][CH2:2][OH:3])[CH2:8][CH2:7][CH2:6][CH2:5]1)=[NH:15])=[CH:18]\[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH3:24]

Participants

8

Reactant 4

HCID 787HydroxylamineHCID 69803Diethyl acetylenedicarboxylateHCID 82115Trimethylsilyl cyanideHCID 567225Cyclopentanone ethylene ketal

Product 1

HCID 178472248HCID 178472248, compound

Reagents, catalysts & solvents 3

HCID 9883512zinc(II)iodideCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A stirred mixture of cyclopentanone ethylene ketal (12.82 g, 100 mmol) and ZnI2 (45 mg, catalytic) was placed in water bath and to this was added trimethylsilyl cyanide (13.35 mL, 100 mmol) via syringe over 10 min. After 16 h, EtOH (100 mL) followed by 50% aqueous hydroxylamine (6.43 mL, 100 mmol) was added and stirred at 80° C. for 2 h. Then, the reaction mixture was cooled in ice-water bath and diethyl acetylenedicarboxylate (16 mL, 100 mmol) was added over 5 min. The cooling bath was removed and the reaction stirred for 4 h at room temperature then concentrated to give the title compound as a dark-brown oil LRMS (M+H) calcd for C16H27N2O7: 359.2; found: 359.2.

Workup

  1. additionwas added
  2. customThe cooling bath was removed
  3. stirringthe reaction stirred for 4 h at room temperature
  4. concentrationthen concentrated

Sources & evidence

ORD record
ord-611656a3830d4400aaf4d606aa65abd8
Source dataset
uspto-grants-2011_02
Patent number
US07893055B2

Reaction notes

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