Triethylamine → Tert-butyl 4-(2,5-dibromopentanamido)piperidine-1-carboxylate

HRID 407894노트

반응식

HRID 407894 반응식
[Br:1][CH:2]([CH2:6][CH2:7][CH2:8][Br:9])[C:3](Br)=[O:4].C(N(CC)CC)C.[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([NH2:30])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>C(Cl)Cl>[Br:1][CH:2]([CH2:6][CH2:7][CH2:8][Br:9])[C:3]([NH:30][CH:27]1[CH2:26][CH2:25][N:24]([C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:23])[CH2:29][CH2:28]1)=[O:4]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 111630822,5-dibromopentanoyl Bromide

생성물 1

HCID 67469892Tert-butyl 4-(2,5-dibromopentanamido)piperidine-1-carboxylate수율 90.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of crude 2,5-dibromopentanoyl bromide (6.50 g, 20 mmol) and triethylamine (3.06 g, 30.2 mmol) in CH2Cl2 (40 mL) cooled to 0° C. was added tert-butyl-4-aminopiperidine-1-carboxylate (4.23 g, 21.1 mmol) in one portion. The reaction was allowed to stir for 4 hours at which point the reaction was quenched by the addition of saturated aqueous NaHCO3 (5 mL) and CH2Cl2 (10 mL). The organic layer was separated and the aqueous layer washed with additional CH2Cl2 (3×15 mL). The combined organic layers were dried with MgSO4 and concentrated. The crude material was purified over silica gel (3:1 hexanes/EtOAc) to give tert-butyl 4-(2,5-dibromopentanamido)piperidine-1-carboxylate (8.00 g, 90%) as a white solid.

후처리

  1. customwas quenched by the addition of saturated aqueous NaHCO3 (5 mL) and CH2Cl2 (10 mL)
  2. customThe organic layer was separated
  3. washthe aqueous layer washed with additional CH2Cl2 (3×15 mL)
  4. dry with materialThe combined organic layers were dried with MgSO4
  5. concentrationconcentrated
  6. customThe crude material was purified over silica gel (3:1 hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-4f4be41b91b94cc4b110d48bc0d9419c
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754226B2

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