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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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HRID 133123 반응식
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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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887
Methanol
용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d0d84e43843d4c4b8ec87a261fa8794a
출처 데이터셋
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07390798B2

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