Isovanillin → 1-(3-hydroxy-4-methoxybenzyl)-4-[{N-(3-(trifluoromethyl)benzoyl)glycyl}aminomethyl]piperidine
Reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][CH:22]=1)[C:6]([NH:8][CH2:9][C:10]([NH:12][CH2:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)=[O:11])=[O:7].[OH:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH:29]=O.[BH3-]C#N.[Na+]>CC(O)=O.CO>[OH:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH2:29][N:17]1[CH2:18][CH2:19][CH:14]([CH2:13][NH:12][C:10](=[O:11])[CH2:9][NH:8][C:6](=[O:7])[C:5]2[CH:20]=[CH:21][CH:22]=[C:3]([C:2]([F:1])([F:23])[F:24])[CH:4]=2)[CH2:15][CH2:16]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 4-[{N-(3-(trifluoromethyl)benzoyl)glycyl}aminomethyl]piperidine (20.0 mg, 0.058 mmol) and 3-hydroxy-4-methoxybenzaldehyde (33 mg) in 5% CH3COOH/CH3OH (1.0 mL) was added NaBH3CN (16.5 mg) in 5% CH3COOH/CH3OH (1.0 mL). The reaction mixture was stirred at 60° C. for 15 h. The reaction mixture was loaded onto Variant™ SCX column and washed with CH3OH (15 mL). Product was eluted using 2 N NH3-CH3OH (5 mL) and the eluant was concentrated to afford 1-(3-hydroxy-4-methoxybenzyl)-4-[{N-(3-(trifluoromethyl)benzoyl)glycyl}aminomethyl]piperidine (Compound No. 1452) (25.8 mg, 92%): The purity was determined by RPLC/MS (91%); ESI/MSm/e 480 (M++H, C24H28F3N3O4).
Workup
- washwashed with CH3OH (15 mL)
- washProduct was eluted
- concentrationthe eluant was concentrated
Sources & evidence
- ORD record
- ord-b8c0f279c7874b01be9da2e7eafd4e35
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06362177B1
Reaction notes
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