Acetic Acid → (3-Benzylamino-phenyl)-carbamic acid tert-butyl ester

HRID 386476Notes

Reaction equation

HRID 386476 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O)(=O)C.[BH4-].[Na+]>O1CCCC1>[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 4311764Sodium borohydrideHCID 12877220tert-butyl N-(3-aminophenyl)carbamate

Product 1

HCID 67229700(3-Benzylamino-phenyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (3-amino-phenyl)-carbamic acid tert-butyl ester (1 g, 4.8 mmol), benzaldehyde (0.54 ml, 5.3 mmol) and acetic acid (0.41 ml, 7.2 mmol) in dry tetrahydrofuran (30 ml) were stirred at room temperature for 2 hrs. Sodium borohydride (0.172 g, 4.5 mmol) was added and the reaction stirred at room temperature overnight. The reaction mixture was quenched with water (50 ml) and extracted with dichloromethane (3×50 ml). The combined organics were dried (magnesium sulphate), concentrated in vacuo and the crude residue purified by flash column chromatography (SiO2) eluting with ethyl acetate to afford the title compound as an off white solid (1.27 g, 89%) HPLC retention time 6.4 min. Mass spectrum (ES+) m/z 198 (M+H-BOC)

Workup

  1. customThe reaction mixture was quenched with water (50 ml)
  2. extractionextracted with dichloromethane (3×50 ml)
  3. dry with materialThe combined organics were dried (magnesium sulphate)
  4. concentrationconcentrated in vacuo
  5. customthe crude residue purified by flash column chromatography (SiO2)
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-6d428428c64741a0a9545bbc31f9dadf
Source dataset
uspto-grants-2013_02
Patent number
US08372840B2

Reaction notes

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