Ammonia → Benzyl 4-hydrazinylpiperidine-1-carboxylate

HRID 75594노트

반응식

HRID 75594 반응식
[C:1]([N:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].O.[NH2:19][NH2:20].[BH4-].[Na+].N>CO.C(Cl)Cl>[CH2:4]([O:3][C:1]([N:11]1[CH2:16][CH2:15][CH:14]([NH:19][NH2:20])[CH2:13][CH2:12]1)=[O:2])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

참가 물질

7

반응물 4

HCID 222AmmoniaHCID 24654Hydrazine hydrate (1:1)HCID 643496Benzyl 4-oxopiperidine-1-carboxylateHCID 4311764Sodium borohydride

생성물 1

HCID 21098319Benzyl 4-hydrazinylpiperidine-1-carboxylate수율 58%

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 6344Dichloromethane용매

실험 절차

A solution of 1-CBZ-4-piperidone (2.92 g, 12.5 mmol) and hydrazine hydrate (2.01 mL, 18.8 mmol) in MeOH (25 mL) was stirred at 50° C. for 30 min, then cooled to RT and NaBH4 (1.18 g, 31.3 mmol) added (CARE: gas evolution and exotherm to −45° C.). The solution was stirred at RT for 30 min, then 50° C. for 18 h. The cooled solution was concentrated in vacuo, suspended in water (25 mL) and extracted with DCM (2×25 mL). The combined organics were passed through a hydrophobic frit and concentrated in vacuo to leave a clear oil. FCC, using 0-10% [2H NH3 in MeOH] in DCM, gave the title compound as a clear oil (1.80 g, 58%). LCMS (Method 3): Rt 2.03 min, m/z 250 [MH+].

후처리

  1. wait50° C. for 18 h
  2. concentrationThe cooled solution was concentrated in vacuo
  3. extractionextracted with DCM (2×25 mL)
  4. concentrationconcentrated in vacuo
  5. customto leave a clear oil

출처 및 근거

ORD 기록
ord-b50190cd3b0a48b7bed0247d2c885e45
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835431B2

반응 노트

불러오는 중…