Sodium Bicarbonate → HCID 178453890, 화합물

HRID 1909358노트

반응식

HRID 1909358 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[C:4]=2[O:3][CH2:2]1.[C:16]([O:20][C:21](=[O:32])[NH:22][C@H:23]1[CH2:28][CH2:27][C@H:26]([CH2:29][CH:30]=O)[CH2:25][CH2:24]1)([CH3:19])([CH3:18])[CH3:17].C(=O)(O)[O-].[Na+]>ClCCl.CO>[C:16]([O:20][C:21](=[O:32])[NH:22][C@H:23]1[CH2:24][CH2:25][C@H:26]([CH2:29][CH2:30][N:13]2[CH2:14][CH2:15][CH:10]([C:9]3[C:4]4[O:3][CH2:2][O:1][C:5]=4[CH:6]=[CH:7][CH:8]=3)[CH2:11][CH2:12]2)[CH2:27][CH2:28]1)([CH3:19])([CH3:18])[CH3:17]

참가 물질

6

반응물 3

HCID 516892Sodium BicarbonateHCID 706572904-Benzo[1,3]dioxol-4-yl-piperidineHCID 178453924HCID 178453924, 화합물

생성물 1

HCID 178453890HCID 178453890, 화합물수율 100.3%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 4-Benzo[1,3]dioxol-4-yl-piperidine (0.680 g, 3.31 mmol,) in dichloromethane (35 ml) and methanol (1 ml) was added at room temperature commercially available trans-tert-butyl-4-(2-oxoethyl)-cyclohexylcarbamate (1.04 g, 4.31 mmol) and the solution was allowed to stir for 120 min. Sodium triacetoxyboron hydride (1.26 g, 5.96 mmol) was added portion wise and the mixture was allowed to stir for 16 h at room temperature. The solution was poured into saturated sodium bicarbonate solution (15 ml) and extracted with dichloromethane (2×20 ml). The combined organic layers were dried (MgSO4) and evaporated. The crude material was purified by flash chromatography on silica gel The crude material was purified by flash chromatography (methanol in dichloromethane 0-10%) to yield trans-{4-[2-(4-Benzo[1,3]dioxol-4-yl-piperidin-1-yl)-ethyl]-cyclohexyl}-carbamic acid tert-butyl ester as a white solid (1.43 g, 74%), MS (ISP) m/z=431.5 [(M+H)+].

후처리

  1. stirringto stir for 16 h at room temperature
  2. extractionextracted with dichloromethane (2×20 ml)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. customevaporated
  5. customThe crude material was purified by flash chromatography on silica gel The crude material
  6. customwas purified by flash chromatography (methanol in dichloromethane 0-10%)

출처 및 근거

ORD 기록
ord-8a3339f7aa444be095b68d24d54f52cc
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598357B2

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