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

HRID 407894ノート

反応式

HRID 407894 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-4f4be41b91b94cc4b110d48bc0d9419c
出典データセット
uspto-grants-2014_06
特許番号
US08754226B2

反応ノート

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