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Sodium Bicarbonate → Ethyl 1-((1,1-dimethylethoxy)carbonyl)-3,6-dihydro-4(2H)-pyridineacetate

HRID 1374141
ノート
印刷プレビュー

反応式

HRID 1374141 の反応式
[CH2:1]([O:3][C:4](=[O:19])[CH:5]=[C:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)[CH3:2].C(OC(N1CCC(=O)CC1)=O)(C)(C)C.C([N-]C(C)C)(C)C.[Li+].C(=O)([O-])O.[Na+]>O1CCCC1.C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH:7]=1)[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 516892Sodium BicarbonateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 2724682Lithium diisopropylamideHCID 10333298tert-Butyl 4-(2-Ethoxy-2-oxoethylidene)piperidine-1-carboxylate

生成物 1

HCID 9970303Ethyl 1-((1,1-dimethylethoxy)carbonyl)-3,6-dihydro-4(2H)-pyridineacetate収率 109.7%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒
HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 300 mg of (1-tert-butoxycarbonylpiperidin-4-ylidene)acetic acid ethyl ester (which had been prepared by Horner-Wittig reaction of commercially available 1-tert-butoxycarbonyl-4-piperidone and triethyl phosphonoacetate by the method known per se) in 30 ml of tetrahydrofuran was cooled to −78° C., to which 1.3 ml of a tetrahydrofuran solution (1.5 M) of lithium diisopropylamide was added and stirred for 15 minutes. Thereafter 150 μl of acetic acid was added, and the system was warmed up to room temperature, over an hour. The reaction liquid, to which saturated aqueous sodium hydrogencarbonate solution was added, was extracted with chloroform. The chloroform layer was dried over sodium sulfate and the solvent was distilled off therefrom to provide 329 mg of (1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridin-4-yl)acetic acid ethyl ester. This ester was dissolved in 10 ml of tetrahydrofuran, cooled to 0° C., and to which 80 mg of lithium aluminium hydride was added. The reaction liquid was stirred for 15 minutes and to which an excessive amount of sodium sulfate decahydrate was added, followed by 2 hours' stirring at room temperature. The insoluble matter was filtered off, and the filtrate was concentrated to provide 228 mg of 2-(1-tert-butoxycarbonyl-1,2,5,6-tetrahydropyridin-4-yl)ethanol.

後処理

  1. additionwas added
  2. customThe reaction liquid
  3. extractionwas extracted with chloroform
  4. dry with materialThe chloroform layer was dried over sodium sulfate
  5. distillationthe solvent was distilled off

出典と根拠

ORDレコード
ord-6d24847997434ff7b2a6c9fec2ea3863
出典データセット
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07164024B2

反応ノート

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