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Acetic Acid → (+/-)Tert-butyl 7-(((6-methylpyridin-2-yl)amino)methyl)-8-azaspiro[4.5]decane-8-carboxylate

HRID 536594
ノート
印刷プレビュー

反応式

HRID 536594 の反応式
[CH:1]([CH:3]1[N:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:10][C:5]2([CH2:9][CH2:8][CH2:7][CH2:6]2)[CH2:4]1)=O.C(O)(=O)C.[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[N:26]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C.C([O-])(O)=O.[Na+]>[CH3:31][C:27]1[N:26]=[C:25]([NH:24][CH2:1][CH:3]2[N:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:10][C:5]3([CH2:9][CH2:8][CH2:7][CH2:6]3)[CH2:4]2)[CH:30]=[CH:29][CH:28]=1
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 176Acetic AcidHCID 157652-Amino-6-methylpyridineHCID 5049666Sodium triacetoxyborohydrideHCID 86664866(+/-)Tert-butyl 7-formyl-8-azaspiro[4.5]decane-8-carboxylate2 回

生成物 1

HCID 66848215(+/-)Tert-butyl 7-(((6-methylpyridin-2-yl)amino)methyl)-8-azaspiro[4.5]decane-8-carboxylate収率 48.3%

試薬・触媒・溶媒 2

HCID 63651,1-Dichloroethane溶媒
HCID 516892Sodium Bicarbonate溶媒

実験手順

(±)tert-butyl 7-formyl-8-azaspiro[4.5]decane-8-carboxylate (Intermediate 72, 2 g, 7.48 mmol) was dissolved in dichloroethane (25 ml), then acetic acid (5 eq) and 2-amino 6 picoline (810 mg, 7.48 mmol) were added. After 3 hours at room temperature NaBH(OAc)3 (2.53 g, 11.96 mmol) was added and the reaction was maintained under stirring at room temperature for 18 hours. The reaction was poured in aqueous NaHCO3 and extracted with ethylacetate. The organic layers were combined, dried (Na2SO4) and concentrated under vacuum; the crude was then purified by silica gel column chromatography (petroleum ether/ethyl acetate=9/1) to obtain 1.3 g of intermediate as colourless oil.

後処理

  1. temperaturethe reaction was maintained
  2. extractionextracted with ethylacetate
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under vacuum
  5. customthe crude was then purified by silica gel column chromatography (petroleum ether/ethyl acetate=9/1)

出典と根拠

ORDレコード
ord-f82197d65d3f4404bebfa01b26061eea
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08859608B2

反応ノート

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