Diisopropylethylamine → tert-butyl (3S)-3-[(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperidin-1-yl)methyl]piperidine-1-carboxylate

HRID 603238노트

반응식

HRID 603238 반응식
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:10][C:11]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[O:12])[CH:6]=[CH:7][C:8]=1[Cl:9].C(N(C(C)C)CC)(C)C.[CH:28]([C@@H:30]1[CH2:35][CH2:34][CH2:33][N:32]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:31]1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:2][C:3]1[CH:4]=[C:5]([NH:10][C:11]([CH:13]2[CH2:14][CH2:15][N:16]([CH2:28][C@@H:30]3[CH2:35][CH2:34][CH2:33][N:32]([C:36]([O:38][C:39]([CH3:40])([CH3:42])[CH3:41])=[O:37])[CH2:31]3)[CH2:17][CH2:18]2)=[O:12])[CH:6]=[CH:7][C:8]=1[Cl:9]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 42325667tert-Butyl (3R)-3-formylpiperidine-1-carboxylateHCID 54595048N-(3,4-dichlorophenyl)piperidine-4-carboxamide hydrochloride

생성물 1

HCID 57656896tert-butyl (3S)-3-[(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperidin-1-yl)methyl]piperidine-1-carboxylate수율 100%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a mixture of N-(3,4-dichlorophenyl)piperidine-4-carboxamide hydrochloride (1.55 g) in dichloromethane (100 mL) was added di-iso-propylethylamine (1.3 mL). The solution was stirred for 15 minutes after which tert-butyl (3R)-3-formylpiperidine-1-carboxylate (1.17 g) and sodium triacetoxyborohydride (1.59 g) was added. The reaction was stirred at room temperature overnight. The reaction mixture was partitioned between dichloromethane and water and the aqueous layer extracted with dichloromethane. The combined organic layers were washed with brine, dried over magnesium sulfate and evaporated to give the title compound as a white foam (2.34 g, 100%).

후처리

  1. additionwas added
  2. customThe reaction mixture was partitioned between dichloromethane and water
  3. extractionthe aqueous layer extracted with dichloromethane
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

출처 및 근거

ORD 기록
ord-5db280a4c7c04be493b5347248068eac
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906645B2

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