2-Nitrobenzaldehyde → benzyl (S)-4-[2-(2-nitrobenzylamino)-1-propoxy]benzoate

HRID 350575Notes

Reaction equation

HRID 350575 reaction equation
[NH2:1][C@@H:2]([CH3:21])[CH2:3][O:4][C:5]1[CH:20]=[CH:19][C:8]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])=[CH:7][CH:6]=1.[N+:22]([C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[CH:27]=O)([O-:24])=[O:23].[BH3-]C#N.[Na+]>CO.CC(O)=O>[N+:22]([C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[CH2:27][NH:1][C@@H:2]([CH3:21])[CH2:3][O:4][C:5]1[CH:20]=[CH:19][C:8]([C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])=[CH:7][CH:6]=1)([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 111012-NitrobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 86587801benzyl (S)-4-(2-amino-1-propoxy)benzoate

Product 1

HCID 86587803benzyl (S)-4-[2-(2-nitrobenzylamino)-1-propoxy]benzoateYield 42.1%

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanolSolvent

Procedure

To a cooled (0° C.) solution of benzyl (S)-4-(2-amino-1-propoxy)benzoate (1.50 g, 5.26 mmol) and 2-nitrobenzaldehyde (0.87 g, 5.76 mmol) in MeOH—AcOH (16 ml, 15:1, v/v) was added NaBH3CN (1.65 g, 26.3 mmol) and the reaction mixture was stirred at room temperature overnight. The mixture was quenched by sat. NaHCO3 and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4 and evaporated. The residue was purified by column chromatography on silica gel with CHCl3 to 5% MEOH in CHCl3 as eluent to give benzyl (S)-4-[2-(2-nitrobenzylamino)-1-propoxy]benzoate (931 mg, 42%) as a yellow oil. 1H-NMR (CDCl3) δ 1.21 (d, J=6.4 Hz, 3 H), 3.13–3.18 (m, 1 H), 3.88–3.97 (m, 2 H), 4.06–4.20 (m, 2 H), 5.34 (s, 2 H), 6.89–6.94 (m, 2 H), 7.29–7.65 (m, 8 H), 7.94–8.03 (m, 3 H); MS (FAB) m/z 421 (M++1).

Workup

  1. customThe mixture was quenched by sat. NaHCO3
  2. extractionextracted with EtOAc
  3. washThe extract was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel with CHCl3 to 5% MEOH in CHCl3 as eluent

Sources & evidence

ORD record
ord-8a52be346e2e4ab0af9f4492108e1a4d
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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