Hydroxyamine hydrochloride → HCID 58504342, compound

HRID 1941876Notes

Reaction equation

HRID 1941876 reaction equation
[C:1]([C:3]1[CH:17]=[CH:16][C:6]([CH2:7][N:8]2[CH2:11][CH:10]([C:12]([O:14][CH3:15])=[O:13])[CH2:9]2)=[CH:5][CH:4]=1)#[N:2].Cl.[NH2:19][OH:20].C(=O)(O)[O-].[Na+]>CO>[OH:20]/[N:19]=[C:1](/[C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH2:9][CH:10]([C:12]([O:14][CH3:15])=[O:13])[CH2:11]2)=[CH:16][CH:17]=1)\[NH2:2]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 66996118HCID 66996118, compound

Product 1

HCID 58504342HCID 58504342, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 1-(4-cyanobenzyl)azetidine-3-carboxylate (760 mg, 3.30 mmol), hydroxylamine hydrochloride (459 mg, 6.60 mmol) and sodium bicarbonate (1109 mg, 13.20 mmol) in MeOH (4.9 mL) was heated to reflux for 2.5 hr. After cooling to rt, the reaction mixture was filtered and the filtrate was concentrated to a residue that was partitioned between EtOAc (75 mL) and water (50 mL). The aqueous layer was extracted with EtOAc (75 mL) and the combined organic layers were dried (MgSO4) and concentrated to afford (Z)-methyl 1-(4-(N′-hydroxycarbamimidoyl)benzyl)azetidine-3-carboxylate (470 mg, 1.785 mmol) as a colorless foam. MS:(M+H)=264.28. 1H NMR (400 MHz, CDCl3) δ ppm 3.30-3.39 (m, 3H) 3.54 (m, 2H) 3.64 (s, 2H) 3.71 (s, 3H) 4.86 (brs, 2H) 7.31 (d, J=8.3 Hz, 2H) 7.57 (d, J=8.3 Hz, 2H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2.5 hr
  3. filtrationthe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated to a residue that
  5. customwas partitioned between EtOAc (75 mL) and water (50 mL)
  6. extractionThe aqueous layer was extracted with EtOAc (75 mL)
  7. dry with materialthe combined organic layers were dried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-99e4c4020d364d908cc1406af6eacbd2
Source dataset
uspto-grants-2013_03
Patent number
US08389509B2

Reaction notes

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