Triethylamine → methyl N-(BOC)-8-aminomethyl-5,6,7,8-tetrahydro-2-naphthoate

HRID 1417905Notes

Reaction equation

HRID 1417905 reaction equation
[NH2:1][CH2:2][CH:3]1[C:12]2[CH:11]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:9]=[CH:8][C:7]=2[CH2:6][CH2:5][CH2:4]1.C(N(CC)CC)C.[C:24]([O:28][C:29](ON=C(C1C=CC=CC=1)C#N)=[O:30])([CH3:27])([CH3:26])[CH3:25].C(OCC)(=O)C>O1CCCC1>[C:29]([NH:1][CH2:2][CH:3]1[C:12]2[CH:11]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:9]=[CH:8][C:7]=2[CH2:6][CH2:5][CH2:4]1)([O:28][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:30]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 14756556Methyl 8-(aminomethyl)-5,6,7,8-tetrahydronaphthalene-2-carboxylate

Product 1

HCID 19359193methyl N-(BOC)-8-aminomethyl-5,6,7,8-tetrahydro-2-naphthoateYield 47.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 8-aminomethyl-5,6,7,8-tetrahydro-2-naphthoate (0.78 g, 0.0036 mol) and triethylamine (0.55 mL, 0.40 g, 0.004 mol) in aqueous tetrahydrofuran (50%, 75 mL) was added, portionwise as a solid, 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile (0.99 g, 0.004 mol). All was stirred at ambient temperature over 3 hours. The solution was concentrated to half volume and extracted with diethylether. The aqueous layer was then acidified to a pH of 1.0 using hydrochloric acid (1N) and then extracted with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate and evaporated to dryness under reduced pressure. The residue was purified by flash chromatography using hexane:ethyl acetate::8:2 to give methyl N-(BOC)-8-aminomethyl-5,6,7,8-tetrahydro-2-naphthoate (0.54 g, 0.0017 mol, 47%) as a white solid. mp=72°-80° C.; 1H NMR (DMSO) d 13.8 (s, 1H), 7.8-7.65 (m, 3H), 7.6-7.5 (m, 3H), 7.25-7.20 (m, 1H), 7.15-7.05 (m, 1H), 3.9-3.8 (m, 1H), 3.2-2.8 (m, 4H), 1.8-1.6 (m, 3H), 1.4 (s, 6H).

Workup

  1. concentrationThe solution was concentrated to half volume
  2. extractionextracted with diethylether
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-373dab26ee6f4d10b8c088fc3c6bcb03
Source dataset
uspto-grants-1999_03
Patent number
US05879657

Reaction notes

Loading…