Hydroxylamine → HCID 58044110, compound

HRID 1772129Notes

Reaction equation

HRID 1772129 reaction equation
C1(C(=[N:14][C:15]2[N:20]=[CH:19][C:18]([CH:21]3[CH2:24][N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:22]3)=[CH:17][CH:16]=2)C2C=CC=CC=2)C=CC=CC=1.NO.O>CO>[NH2:14][C:15]1[N:20]=[CH:19][C:18]([CH:21]2[CH2:22][N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:24]2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 962WaterHCID 86697066tert-Butyl 3-(6-(Diphenylmethyleneamino)pyridin-3-yl)azetidine-1-carboxylate

Product 1

HCID 58044110HCID 58044110, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 250-mL round-bottomed flask equipped with a magnetic stirrer was charged with 117b (2.44 g, 5.91 mmol), methanol (80 mL), 50% hydroxylamine in water (390 mg, 11.8 mmol) and the reaction was stirred at room temperature for 4 h. After this time, the reaction mixture was concentrated, and the resulting residue was purified by column chromatography to afford an 86% yield (1.27 g) of 117c as a yellow solid: mp 103-104° C.; 1H NMR (500 MHz, CDCl3) δ 7.94 (d, 1H, J=2.0 Hz), 7.49 (dd, 1H, J=8.5, 2.5 Hz), 6.53 (d, 1H, J=8.5 Hz), 4.48 (br s, 2H), 4.30 (t, 2H, J=8.5 Hz), 3.88 (dd, 2H, J=8.5, 4.5 Hz), 3.62 (m, 1H), 1.44 (s, 9H); MS (ESI+) m/z 249.9 (M+H).

Workup

  1. customA 250-mL round-bottomed flask equipped with a magnetic stirrer
  2. concentrationAfter this time, the reaction mixture was concentrated
  3. customthe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-531b3889cd5145f18b6f5be9ad3ea4c7
Source dataset
uspto-grants-2016_02
Patent number
US09249123B2

Reaction notes

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