Sodium Hydroxide → Tert-butyl 2-(1-(4-bromophenyl)piperidin-4-yloxy)acetate

HRID 57592ノート

反応式

HRID 57592 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-].[Na+].Br[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][CH:11]([O:14][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 235052161-(4-Bromophenyl)piperidin-4-ol

生成物 1

HCID 86717376Tert-butyl 2-(1-(4-bromophenyl)piperidin-4-yloxy)acetate収率 83.2%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

Tetrabutylammonium bromide (1.06 g, 3.3 mmol) is added to a solution of 1-(4-bromophenyl)piperidin-4-ol (2.56 g, 10 mmol) in toluene (30 mL). The reaction mixture was cooled to 0° C. and aq. 35% sodium hydroxide (30 mL) was added followed by a drop-wise addition of tert-butyl bromoacetate (2.92 g, 15 mmol). The mixture was then allowed to reach room temperature and was stirred for 17 hours at this temperature. The layers were separated and the organic layer was washed twice with water (4 mL), dried over sodium sulfate, concentrated under vacuum and co-evaporated with petroleum ether. Purification of the crude material by flash column chromatography on silica gel (0-20% ethyl acetate in petroleum ether) yielded the desired pure material 3.08 g as pale yellow solid. MS (m/z): 372 (M+2)+

後処理

  1. customto reach room temperature
  2. customThe layers were separated
  3. washthe organic layer was washed twice with water (4 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum and co-evaporated with petroleum ether
  6. customPurification of the crude material by flash column chromatography on silica gel (0-20% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-e0555bf4748e40bda55444f47f18849a
出典データセット
uspto-grants-2016_09
特許番号
US09434726B2

反応ノート

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