Methanol → di-tert-butyl 1-(3,3-dimethyl-1H-inden-5-yl)hydrazine-1,2-dicarboxylate

HRID 2271436ノート

反応式

HRID 2271436 の反応式
[CH3:1][C:2]1([CH3:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.C([Li])CCC.[N:17]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[N:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].CO>O1CCCC1>[CH3:1][C:2]1([CH3:11])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N:17]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[NH:18][C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH:9]=2)[CH:4]=[CH:3]1.[CH3:1][C:2]1([CH3:11])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N:17]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[NH:18][C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH:9]=2)[CH2:4][CH2:3]1

参加物

7

反応物 4

HCID 887MethanolHCID 786242,3-dihydro-1,1-dimethyl-1H-indeneHCID 97268Di-tert-butyl azodicarboxylateHCID 178418339Butyllithium

生成物 2

HCID 59615676di-tert-butyl 1-(3,3-dimethyl-1H-inden-5-yl)hydrazine-1,2-dicarboxylate収率 37.2%HCID 67128578Di-tert-butyl 1-(3,3-dimethyl-inden-5-yl)hydrazine-1,2-dicarboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

6-Bromo-1 μl-dimethyl-indan (prepared by using a well-known method: patent application WO2005066115) 4a (4.32 g, 19.27 mmol) was dissolved in 40 mL of tetrahydrofuran and then butyllithium (15.67 mL, 1.6 M, 25.05 mmol) was added dropwise at −78° C. After the reaction mixture was reacted for 40 minutes, a solution of di-tert-butyl azodicarboxylate (5.32 g, 23.12 mmol) in 30 mL of tetrahydrofuran was then added. The reaction mixture was reacted for another 3 hours at −78° C. The reaction mixture was added with 5 mL of methanol, then warmed up to room temperature and filtered by silica gel. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography to obtain the title compound di-tert-butyl 1-(3,3-dimethyl-1H-inden-5-yl)hydrazine-1,2-dicarboxylate 4b (2.70 g, yield 37.2%) as a yellow solid.

後処理

  1. customAfter the reaction mixture was reacted for 40 minutes
  2. customThe reaction mixture was reacted for another 3 hours at −78° C
  3. filtrationfiltered by silica gel
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-9b2ffffdae794531a54d4ca3ee996b88
出典データセット
uspto-grants-2015_09
特許番号
US09120762B2

反応ノート

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