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

HRID 133123
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 133123
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
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Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d0d84e43843d4c4b8ec87a261fa8794a
Quelldatensatz
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07390798B2

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