Chloroiodomethane → (4S)-6-Azaspiro[2.5]octan-4-ol hydrochloride

HRID 559329ノート

反応式

HRID 559329 の反応式
[CH2:1]([Zn]CC)C.[Cl:6]CI.C(OC([N:16]1[CH2:21][CH2:20][C:19](=[CH2:22])[CH:18]([OH:23])[CH2:17]1)=O)(C)(C)C>ClCCCl>[ClH:6].[CH2:22]1[C:19]2([CH2:20][CH2:21][NH:16][CH2:17][C@H:18]2[OH:23])[CH2:1]1

参加物

5

反応物 3

HCID 11644ChloroiodomethaneHCID 10584700tert-Butyl 3-hydroxy-4-methylidenepiperidine-1-carboxylateHCID 178418750HCID 178418750、化合物

生成物 1

HCID 44541812(4S)-6-Azaspiro[2.5]octan-4-ol hydrochloride収率 36,664.699%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of diethylzinc (1.1 M solution in toluene, 37.5 ml, 0.04 mmol) in 1,2-dichloroethane (80 ml) at 0° C. was added chloroiodomethane (5.99 ml, 0.08 mmol) under Ar. This mixture was stirred for 15 minutes before a solution of 3-hydroxy-4-methylene-piperidine-1-carboxylic acid tert-butyl ester (J. Org. Chem. 2001, 66, 2487) (4.19 g, 19.6 mmol) in 1,2-dichloroethane (10 ml) was added, after which time the reaction was stirred for 0.5 h at 0° C. and then allowed to reach room temperature, stirring for a further 1 h. The reaction was then quenched by addition of saturated aq. ammonium chloride solution, separated, and the organic dried (Na2SO4) and concentrated. Purification by flash column chromatography (ethyl acetate/heptane 2:8-1:1) afforded the title product (2.4 g, 54%) as a crystalline solid MS: 228.2 (MH+).

後処理

  1. additionwas added
  2. customto reach room temperature
  3. stirringstirring for a further 1 h
  4. customThe reaction was then quenched by addition of saturated aq. ammonium chloride solution
  5. customseparated
  6. dry with materialthe organic dried (Na2SO4)
  7. concentrationconcentrated
  8. customPurification by flash column chromatography (ethyl acetate/heptane 2:8-1:1)

出典と根拠

ORDレコード
ord-2e7967a7a7c94bc5bac14bfffe51af8e
出典データセット
uspto-grants-2011_11
特許番号
US08063042B2

反応ノート

読み込み中…