4-Bromoaniline → HCID 67114178、化合物

HRID 1968870ノート

反応式

HRID 1968870 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 67114178HCID 67114178、化合物収率 90%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-44888d82a3464e7d941c0ca29026dd0c
出典データセット
uspto-grants-2013_04
特許番号
US08426414B2

反応ノート

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