Sodium Bicarbonate → (2S,3S)-1-tert-Butoxycarbonyl-3-(5-(1-cyanoethyl)-2-methoxybenzyl)amino-2-phenylpiperidine

HRID 481497

반응식

HRID 481497 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.[C:21]([CH:23]([C:25]1[CH:26]=[CH:27][C:28]([O:33][CH3:34])=[C:29]([CH:32]=1)[CH:30]=O)[CH3:24])#[N:22].[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][CH2:30][C:29]2[CH:32]=[C:25]([CH:23]([C:21]#[N:22])[CH3:24])[CH:26]=[CH:27][C:28]=2[O:33][CH3:34])[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 물질

6

반응물 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 11311934(2S,3S)-3-Amino-1-tert-butoxycarbonyl-2-phenylpiperidineHCID 190664875-(1-Cyanoethyl)-2-methoxybenzaldehyde

생성물 1

HCID 57028229(2S,3S)-1-tert-Butoxycarbonyl-3-(5-(1-cyanoethyl)-2-methoxybenzyl)amino-2-phenylpiperidine수율 103.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred and ice-cooled solution of Compound 17 (160 mg, 0.60 mmol) and Compound 14 (120 mg, 0.60 mmol) in dry CH2Cl2 (5 ml) was added NaBH(OAc)3 (430 mg, 2.0 mmol) in one portion. 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 18 as a yellow oil (280 mg).

후처리

  1. stirringThe 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-6d9f25a64db247fdb285099b400e9bed
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05789423

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