Sodium Chloride → 4-Amino-2(alpha-hydroxybenzyl)-2'-methoxymethoxy-6'-methoxy-biphenyl

HRID 1358116Notes

Reaction equation

HRID 1358116 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:9]=2[O:16][CH2:17][O:18][CH3:19])=[C:4]([C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:3]=1.[BH4-].[Na+].C(Cl)(Cl)Cl.[Na+].[Cl-]>C(O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:9]=2[O:16][CH2:17][O:18][CH3:19])=[C:4]([CH:20]([OH:27])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6212ChloroformHCID 4311764Sodium borohydrideHCID 181885574-Amino-2-benzoyl-2'-methoxymethoxy-6'-methoxy-biphenyl

Product 1

HCID 181891954-Amino-2(alpha-hydroxybenzyl)-2'-methoxymethoxy-6'-methoxy-biphenylYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound of Example 5D (4.84, 13.31 mmol) in ethanol (45 mL) was heated at 65° C. with NaBH4(2.03 g, 53.42 mmol). After 1 hour Chloroform and aqueous NaCl was added. The organic phase was separated, washed with aqueous KHCO3, dried (Na2SO4), filtered and the solvent removed under reduced pressure to provide the titled compound (3.844 g, 80%).

Workup

  1. customThe organic phase was separated
  2. washwashed with aqueous KHCO3
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-cac13647593b46009d3c748982c29a73
Source dataset
uspto-grants-2003_07
Patent number
US06593480B2

Reaction notes

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