Hydroxylamine → 4-Cyanobenzaldehyde

HRID 1941870Notes

Reaction equation

HRID 1941870 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]([O:7]C(C)(C)C)=[O:6])[CH2:2]1.[NH:12]1[CH2:15][CH:14]([C:16](O)=O)[CH2:13]1.C1N=CN(C(N2C=NC=C2)=O)C=1.NO>C(O)(C)(C)C>[NH:1]1[CH2:4][CH:3]([C:5]([OH:7])=[O:6])[CH2:2]1.[CH:5]([C:3]1[CH:2]=[CH:16][C:14]([C:13]#[N:12])=[CH:15][CH:4]=1)=[O:7]

Participants

7

Reactant 4

HCID 787HydroxylamineHCID 682631,1'-CarbonyldiimidazoleHCID 931923-azetidinecarboxylic AcidHCID 21828700tert-Butyl azetidine-3-carboxylate

Product 2

HCID 660424-CyanobenzaldehydeHCID 931923-azetidinecarboxylic Acid

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

tert-Butyl azetidine-3-carboxylate (3.6.1) may be prepared from azetidine-3-carboxylic acid (3.5) via protection of the amine (for example with the CBZ group) followed by esterification of the acid with tert-butyl alcohol in the presence of a coupling reagent (for example CDI) and then removal of the amine protecting group. (Z)-tert-butyl 1-(4-(N′-hydroxycarbamimidoyl)benzyl)azetidine-3-carboxylate (2.1.1) is available from the reaction of tert-butyl azetidine-3-carboxylate (3.6.1) with 4-formylbenzonitrile (4.2) under reducing conditions to give 4.3, which is then reacted with hydroxylamine. Alternatively, compound 4.3 may be prepared by esterification of 4.5, which is obtained from the reaction of azetidine-3-carboxylic acid (3.5) with 4-formylbenzonitrile (4.2) under reducing conditions.

Workup

  1. customremoval of the amine protecting group
  2. custom(Z)-tert-butyl 1-(4-(N′-hydroxycarbamimidoyl)benzyl)azetidine-3-carboxylate (2.1.1) is available from the reaction of tert-butyl azetidine-3-carboxylate (3.6.1) with 4-formylbenzonitrile (4.2) under reducing conditions
  3. customto give 4.3, which

Sources & evidence

ORD record
ord-c48209913bef479c9c3ab186a2ada599
Source dataset
uspto-grants-2013_03
Patent number
US08389509B2

Reaction notes

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