Water → HCID 67188113, compound

HRID 735872Notes

Reaction equation

HRID 735872 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[F:22][C:23]([F:33])([F:32])[C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCCl>[F:22][C:23]([F:32])([F:33])[C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH:1][CH2:2][C:3]2[CH:8]=[CH:7][C:6]([C:9]3[CH:14]=[CH:13][C:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:11][CH:10]=3)=[CH:5][CH:4]=2)=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 679964-(Trifluoromethyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67186538HCID 67186538, compound

Product 1

HCID 67188113HCID 67188113, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of tert-butyl 4′-(aminomethyl)-1,1′-biphenyl-4-carboxylate (2.0 g) and 4-(trifluormethyl)-benzaldehyde (0.88 mL) in DCE (40 mL) was added at once sodium triacetoxyborohydride (1.904 g). The resulting mixture was stirred for 14 h at rt. Water (50 mL) was added and the mixture extracted with DCM (3×). The combined organic layers were washed with water (50 mL), then dried over MgSO4, evaporated off to give a yellow oil. This crude was purified by flash chromatography (c-Hex/AcOEt 4/1) to give the title compound as a white powder (1.30 g, 43%). M+(LC/MS(ESI)): 442.02

Workup

  1. extractionthe mixture extracted with DCM (3×)
  2. washThe combined organic layers were washed with water (50 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated off
  5. customto give a yellow oil
  6. customThis crude was purified by flash chromatography (c-Hex/AcOEt 4/1)

Sources & evidence

ORD record
ord-639526553e4a47d29762787896176cd7
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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