Acetic Acid → (2-Allyl-6-benzylamino-3-hydroxy-phenyl)-(4-isopropyl-phenyl)-methanone

HRID 1046384Notes

Reaction equation

HRID 1046384 reaction equation
[CH2:1]([C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[C:6]([NH2:11])[C:5]=1[C:12]([C:14]1[CH:19]=[CH:18][C:17]([CH:20]([CH3:22])[CH3:21])=[CH:16][CH:15]=1)=[O:13])[CH:2]=[CH2:3].[CH:23](=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([BH3-])#N.[Na+].C(O)(=O)C.Cl>ClCCCl>[CH2:1]([C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[C:6]([NH:11][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:5]=1[C:12]([C:14]1[CH:15]=[CH:16][C:17]([CH:20]([CH3:22])[CH3:21])=[CH:18][CH:19]=1)=[O:13])[CH:2]=[CH2:3]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 45141175(2-Allyl-6-amino-3-hydroxy-phenyl)-(4-isopropyl-phenyl)-methanone

Product 1

HCID 45141177(2-Allyl-6-benzylamino-3-hydroxy-phenyl)-(4-isopropyl-phenyl)-methanone

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 39 mg (0.13 mmol) (2-allyl-6-amino-3-hydroxy-phenyl)-(4-isopropyl-phenyl)-methanone and 13.34 μl (13 mmol) benzaldehyde in 1.3 ml 1,2-dichlorethane and 0.3 g molecular sieves (4 Å pore size) are added after 1 h 13 mg (0.18 mmol) sodium cyanoborohydride and 7.55 μl acetic acid (0.13 mmol). After stirring for 16 h at r.t. 1 M hydrochloric acid is added to destroy the excess of hydride equivalents. By adding 1 M NaOH the mixture is basified. The crude product obtained by extraction with dichloromethane is purified by reversed phase preparative chromatography.

Workup

  1. customto destroy the excess of hydride equivalents
  2. additionBy adding 1 M NaOH the mixture

Sources & evidence

ORD record
ord-75234e216f314082a12d00307af0059e
Source dataset
uspto-grants-2013_10
Patent number
US08569317B2

Reaction notes

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