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

HRID 641849Notes

Reaction equation

HRID 641849 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-2cd2c3149e6540fdb350e87d53b3739c
Source dataset
uspto-grants-2010_04
Patent number
US07696216B2

Reaction notes

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