Ethyl Acetate → 3-[4-(Hydroxyimino-methyl)-phenyl]-azetidine-1-carboxylic acid tert-butyl ester

HRID 1961548Notes

Reaction equation

HRID 1961548 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]=O)=[CH:14][CH:13]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:21][OH:22].C([O-])(=O)C.[Na+].C(OCC)(=O)C>C(O)C.O.CCCCCC>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]=[N:21][OH:22])=[CH:14][CH:13]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 21250649HCID 21250649, compound

Product 1

HCID 766614793-[4-(Hydroxyimino-methyl)-phenyl]-azetidine-1-carboxylic acid tert-butyl esterYield 94.51%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 19096565Water ethanolSolvent

Procedure

To a stirred suspension of 3-(4-Formyl-phenyl)-azetidine-1-carboxylic acid tert-butyl ester (Preparation 38, 6.5 g, 24.904 mmol, 1 equivalents) in ethanol:water (1:1, 120 mL) was added hydroxylamine hydrochloride (2.5 g, 37.356 mmol, 1.5 equivalents) followed by sodium acetate (3.67 g, 44.82 mol, 1.8 eq). Resulting reaction mixture was stirred at room temperature for 0.5 hours. Progress of the reaction was monitored by TLC using 20% ethyl acetate in hexane and visualized in UV light (254 nm). Reference of new spot and starting material was 0.32 and 0.67 respectively. After consumption of starting material, solvents was evaporated under reduced pressure and extracted with DCM (3×25 mL). Evaporation of volatiles provided light yellow solid (6.5 g, 94.51%). LC-MS and 1H NMR was consistent. 1H NMR (400 MHz, DMSO-d6) δ 1.39 (s, 9H), 3.81 (broad s, 3H), 4.42 (broad s, 2H), 7.36 (d, J=8 Hz, 2H), 7.57 (d, J=8 Hz, 2H), 8.12 (s, 1H), 11.19 (s, 1H). LC-MS (m/z):=277.30 (M+H).

Workup

  1. customResulting
  2. customreaction mixture
  3. customAfter consumption of starting material, solvents
  4. customwas evaporated under reduced pressure
  5. extractionextracted with DCM (3×25 mL)
  6. customEvaporation of volatiles

Sources & evidence

ORD record
ord-d96e0417563441b2ae4f930a387c8743
Source dataset
uspto-grants-2013_04
Patent number
US08415310B2

Reaction notes

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