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

HRID 536594
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HRID 536594 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 157652-Amino-6-methylpyridineHCID 5049666Sodium triacetoxyborohydrideHCID 86664866(+/-)Tert-butyl 7-formyl-8-azaspiro[4.5]decane-8-carboxylate2회

생성물 1

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

시약·촉매·용매 2

HCID 63651,1-Dichloroethane용매HCID 516892Sodium Bicarbonate용매

실험 절차

(±)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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f82197d65d3f4404bebfa01b26061eea
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08859608B2

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