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Sodium Bicarbonate → (2S, 3S)-1-tert-Butoxycarbonyl-2-phenyl-3-(5-(2,2,2-trifluoro-1-(trifluoromethyl)ethyl)-2-methoxybenzyl)aminopiperidine

HRID 2269245
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HRID 2269245 반응식
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@H:3]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[F:21][C:22]([F:39])([F:38])[CH:23]([C:28]1[CH:29]=[CH:30][C:31]([O:36][CH3:37])=[C:32]([CH:35]=1)[CH:33]=O)[C:24]([F:27])([F:26])[F:25].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:11]([O:10][C:8]([N:4]1[CH2:5][CH2:6][CH2:7][C@H:2]([NH:1][CH2:33][C:32]2[CH:35]=[C:28]([CH:23]([C:22]([F:39])([F:21])[F:38])[C:24]([F:25])([F:26])[F:27])[CH:29]=[CH:30][C:31]=2[O:36][CH3:37])[C@@H:3]1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:9])([CH3:14])([CH3:13])[CH3:12]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 11311934(2S,3S)-tert-Butyl 3-amino-2-phenylpiperidine-1-carboxylateHCID 186776145-(2,2,2-Trifluoro-1-(trifluoromethyl)ethyl)-2-methoxybenzaldehyde

생성물 1

HCID 15549735(2S, 3S)-1-tert-Butoxycarbonyl-2-phenyl-3-(5-(2,2,2-trifluoro-1-(trifluoromethyl)ethyl)-2-methoxybenzyl)aminopiperidine
수율 103.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred and ice-cooled solution of Compound 12 (100 mg, 0.3 mmol) and Compound 9 (100 mg, 0.3 mmol) in dry CH2Cl2 (10 ml) was added NaBH(OAc)3 (210 mg, 1 mmol) in one portion. After the mixture was stirred at room temperature for 20 hours. The mixture was poured into NaHCO3 aq., and extracted with CH2Cl2. The combined extracts were dried (Na2SO4), and concentrated in vacuo to give Compound 13 as a yellow oil (170 mg).

후처리

  1. stirringAfter the mixture was stirred at room temperature for 20 hours
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-faa1df779fb44fd3b033ead414aea187
출처 데이터셋
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06329396B1

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