4-Methylbenzylamine → (3-{[(4-Methyl-benzyl)-amino]-methyl}-phenyl)-acetic Acid Ethyl Ester

HRID 480317Notes

Reaction equation

HRID 480317 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.[CH2:10]([O:12][C:13](=[O:23])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]=O)[CH:16]=1)[CH3:11].[BH4-].[Na+].C([O-])(O)=O.[Na+]>CO.O>[CH2:10]([O:12][C:13](=[O:23])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][NH:7][CH2:6][C:5]2[CH:8]=[CH:9][C:2]([CH3:1])=[CH:3][CH:4]=2)[CH:16]=1)[CH3:11]

Participants

7

Reactant 4

HCID 660354-MethylbenzylamineHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 23076590Ethyl 2-(3-formylphenyl)acetate

Product 1

HCID 53797538(3-{[(4-Methyl-benzyl)-amino]-methyl}-phenyl)-acetic Acid Ethyl EsterYield 107.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-methylbenzylamine (0.097 mL, 0.76 mmol) and (3-formyl-phenyl)-acetic acid ethyl ester (138 mg, 0.72 mmol) in MeOH (2 mL) was stirred for 3 h at room temperature. The reaction was cooled to 0° C. and NaBH4 (43 mg, 1.15 mmol) was added. After stirring at room temperature for 10 minutes, a 1:1 mixture of saturated aqueous NaHCO3:H2O was added. The product was extracted into CH2Cl2 (3×) and the organic solution was dried over MgSO4, filtered, and concentrated to yield the title compound (231 mg). 1H NMR (400 MHz, CDCl3) δ 7.13-7.30 (m, 8H), 4.14 (q, 2H), 3.83 (d, 4H), 3.78 (s, 2H), 2.34 (s, 3H), 1.25 (t, 3H); MS 298 (M+1).

Workup

  1. extractionThe product was extracted into CH2Cl2 (3×)
  2. dry with materialthe organic solution was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-49f828704d274d40981b5d1e64e2fe88
Source dataset
uspto-grants-2003_11
Patent number
US06649657B2

Reaction notes

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