3-Carboxybenzaldehyde → 3-{[4-(tert-Butoxycarbonyl)piperazin-1-yl]methyl}benzoic acid

HRID 880279Notes

Reaction equation

[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])=O.[N:12]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.[BH3-]C#N.[Na+]>CO>[C:21]([O:20][C:18]([N:12]1[CH2:17][CH2:16][N:15]([CH2:1][C:3]2[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=2)[C:6]([OH:8])=[O:7])[CH2:14][CH2:13]1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

Conditions

Temperature: 27 °C

Procedure

The solution of 3-formylbenzoic acid (300 mg, 1.83 mmol) and tert-butyl piperazine-1-carboxylate (340 mg, 1.83 mmol) in MeOH (10 mL) was stirred at 27° C. for 1 h. Then NaBH3CN (138 mg, 2.19 mmol) was added to the solution and stirred at 27° C. for 6 h. The solution was concentrated and the residue was purified by column to give the title product (320 mg, Yield 50%). LCMS (m/z): 321.2 (M+1).

Workup

concentrationThe solution was concentrated
customthe residue was purified by column

Sources & evidence

ORD record: ord-bd01702e96ad4aa584232d54c323898e
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993555B2

Reaction notes

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