4-Methoxybenzaldehyde → tert-Butyl 3-{[(4-methoxyphenyl)methyl]amino}azetidine-1-carboxylate

HRID 889457Notes

Reaction equation

HRID 889457 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[NH2:11][CH:12]1[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]1.COC1C=CC(CNC2CCC2)=CC=1>CO>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:11][CH:12]2[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 312444-MethoxybenzaldehydeHCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylateHCID 59313984N-[(4-methoxyphenyl)methyl]cyclobutanamine

Product 1

HCID 59313975tert-Butyl 3-{[(4-methoxyphenyl)methyl]amino}azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6A was prepared from 4-methoxybenzaldehyde and tert-butyl 3-aminoazetidine-1-carboxylate following the procedure employed for the preparation of 4A. HPLC: Rt=3.0 min (PHENOMENEX® Luna C18 4.6×30 mm 3 u, 10-90% aqueous methanol containing 0.1% TFA in 2 min; 4 mL/min flow). MS (ES): m/z=293.9 [M+H]+.

Sources & evidence

ORD record
ord-357860474ca14831b888fe7ee6127f6a
Source dataset
uspto-grants-2012_08
Patent number
US08252795B2

Reaction notes

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