N-bromobutanimide → Tert-butyl 4-(3-bromo-2-oxopropyl)piperidine-1-carboxylate

HRID 335259ノート

反応式

HRID 335259 の反応式
C[Si](C)(C)[O:3][C:4](=[CH2:19])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.C(=O)(O)[O-].[Na+].[Br:27]N1C(=O)CCC1=O>C1COCC1>[Br:27][CH2:3][C:4](=[O:19])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1

参加物

5

反応物 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 66994845Tert-butyl 4-(2-(trimethylsilyloxy)allyl)piperidine-1-carboxylate

生成物 1

HCID 22243583Tert-butyl 4-(3-bromo-2-oxopropyl)piperidine-1-carboxylate収率 110%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of tert-butyl 4-(2-(trimethylsilyloxy)allyl)piperidine-1-carboxylate (6.43 g, 20.5 mmol) in THF (100 mL) at 0° C. was added sodium bicarbonate (2.58 g, 30.7 mmol) followed by 1-bromopyrrolidine-2,5-dione (3.65 g, 20.5 mmol). Warmed to ambient temperature and stirred 90 minutes. Partitioned between ether (150 mL) and saturated sodium bicarbonate. The aqueous layer was reextracted with ether (100 mL). The combined organic layers were washed with saturated bicarbonate, brine, dried, and concentrated to afford the title compound (7.2 g, 110% yield) as a yellow oil. Purity was 85% with the major impurity being succinimide. The crude material was used in the next step.

後処理

  1. customPartitioned between ether (150 mL) and saturated sodium bicarbonate
  2. washThe combined organic layers were washed with saturated bicarbonate, brine
  3. customdried
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-b6a96567cc93453095c43d430fa080d7
出典データセット
uspto-grants-2014_11
特許番号
US08883828B2

反応ノート

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