Triethylamine → 7-(4-Butyl-benzylamino)-heptanoic acid methyl ester

HRID 2300414Notes

Reaction equation

HRID 2300414 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:12])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH2:11].[CH2:13]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1)[CH2:14][CH2:15][CH3:16].C(N(CC)CC)C.[BH4-].[Na+]>CO>[CH3:2][O:3][C:4](=[O:12])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:11][CH2:21][C:20]1[CH:23]=[CH:24][C:17]([CH2:13][CH2:14][CH2:15][CH3:16])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 709884-ButylbenzaldehydeHCID 4311764Sodium borohydrideHCID 13807349Methyl 7-aminoheptanoate hydrochloride

Product 1

HCID 541174917-(4-Butyl-benzylamino)-heptanoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 7-amino-heptanoic acid methyl ester hydrochloride, prepared of Preparation 1, (1.12 g, 5.9 mmol), 4-butyl-benzaldehyde (0.915 g, 5.65 mmol) and triethylamine (0.83 mL, 5.98 mmol) in 20 mL MeOH was stirred at room temperature for 3 hours. After cooling to 0° C., NaBH4 (0.342 g, 9.04 mmol) was added and the reaction was stirred for 15 minutes at room temperature. The mixture was quenched with 1:1 NaHCO3:H2O and the MeOH was removed in vacuo. The resulting residue was diluted with CH2Cl2 and the organic solution was washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo to afford the title compound of Step A (1.4 g). 1H NMR (400 MHz, CDCl3) δ 7.08-7.38 (m, 4H), 3.62 (s, 2H), 3.29 (s, 3H), 2.52-2.66 (m, 4H), 2.25 (t, 2H), 1.53-1.63 (m, 6H), 1.25-1.40 (m, 6H), 0.85 (t, 3H); MS 306 (M+1).

Workup

  1. temperatureAfter cooling to 0° C.
  2. stirringthe reaction was stirred for 15 minutes at room temperature
  3. customThe mixture was quenched with 1:1 NaHCO3
  4. customH2O and the MeOH was removed in vacuo
  5. additionThe resulting residue was diluted with CH2Cl2
  6. washthe organic solution was washed with water and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3022d282302b4897b65c91810f0d8e69
Source dataset
uspto-grants-2002_12
Patent number
US06498172B1

Reaction notes

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