4-Bromoaniline → HCID 67114178, 화합물

HRID 1968870노트

반응식

HRID 1968870 반응식
[C:1]([NH:8][C:9]1([CH:14]=O)[CH2:13][CH2:12][CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Br:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[C:4]([O:3][C:1](=[O:2])[NH:8][C:9]1([CH2:14][NH:21][C:20]2[CH:22]=[CH:23][C:17]([Br:16])=[CH:18][CH:19]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1)([CH3:7])([CH3:6])[CH3:5]

참가 물질

5

반응물 3

HCID 78074-BromoanilineHCID 5049666Sodium triacetoxyborohydrideHCID 16217741tert-Butyl (1-formylcyclopentyl)carbamate

생성물 1

HCID 67114178HCID 67114178, 화합물수율 90%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

To a solution of N-Boc-cycloleucinal (5.33 g, 25 mmol) and 4-bromoaniline (4.3 g, 25 mmol) in dichloroethane (160 mL) was added sodium triacetoxyborohydride (10.6 g, 50 mmol) portionwise. After the addition, the resulting mixture was stirred at rt for over night. The reaction mixture was quenched with saturated NaHCO3, and extracted with DCM (4×100 mL). The combined DCM was dried (Na2SO4) and concentrated. The residue was subjected to flash column (10-30% EtOAc in hexane) to give the desired product as a white solid (8.3 g, 90%). MS (MH+ 369 and 371).

후처리

  1. additionAfter the addition
  2. customThe reaction mixture was quenched with saturated NaHCO3
  3. extractionextracted with DCM (4×100 mL)
  4. dry with materialThe combined DCM was dried (Na2SO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-44888d82a3464e7d941c0ca29026dd0c
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08426414B2

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