Acetic Acid → (+/-)-Dimethyl 2-{2-[(4-methoxybenzyl)amino]ethyl}-1,2,3,4-tetrahydronaphthalene-2,6-dicarboxylate

HRID 133123Notes

Reaction equation

HRID 133123 reaction equation
O=[CH:2][CH2:3][C:4]1([C:18]([O:20][CH3:21])=[O:19])[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:14]([O:16][CH3:17])=[O:15])[CH:10]=2)[CH2:5]1.[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=1.CC(O)=O.C([BH3-])#N.[Na+]>CO>[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH:29][CH2:2][CH2:3][C:4]2([C:18]([O:20][CH3:21])=[O:19])[CH2:13][CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[C:9]([C:14]([O:16][CH3:17])=[O:15])[CH:10]=3)[CH2:5]2)=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 754524-MethoxybenzylamineHCID 5003444Sodium cyanoborohydrideHCID 86616923(+/-)-Dimethyl 2-(2-oxoethyl)-1,2,3,4-tetrahydronaphthalene-2,6-dicarboxylate

Product 1

HCID 67525773(+/-)-Dimethyl 2-{2-[(4-methoxybenzyl)amino]ethyl}-1,2,3,4-tetrahydronaphthalene-2,6-dicarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (1)-dimethyl 2-(2-oxoethyl)-1,2,3,4-tetrahydronaphthalene-2,6-dicarboxylate from Step C (436 mg, 1.50 mmol), 4-methoxybenzylamine (247 mg, 1.80 mmol), and AcOH (0.206 mL, 3.60 mmol) was stirred in MeOH (10 mL) at ambient temperature for 5 min, then sodium cyanoborohydride (113 mg, 1.80 mmol) was added. After 18 h, the mixture was concentrated in vacuo, and the residue was partitioned between saturated aqueous NaHCO3 (10 mL) and CH2Cl2 (20 mL). The aqueous phase was extracted further with CH2Cl2 (10 mL), and the combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound in sufficient purity for use in the next step. MS: m/z=412 (M+1).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe residue was partitioned between saturated aqueous NaHCO3 (10 mL) and CH2Cl2 (20 mL)
  3. extractionThe aqueous phase was extracted further with CH2Cl2 (10 mL)
  4. dry with materialthe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d0d84e43843d4c4b8ec87a261fa8794a
Source dataset
uspto-grants-2008_06
Patent number
US07390798B2

Reaction notes

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