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

HRID 133123
ノート
印刷プレビュー

反応式

HRID 133123 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d0d84e43843d4c4b8ec87a261fa8794a
出典データセット
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07390798B2

反応ノート

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