Lithium Hexamethyldisilazide → HCID 67271943、化合物

HRID 597841

反応式

HRID 597841 の反応式
[C:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:5][CH2:4]1)#[N:2].Cl[CH2:20][O:21][CH2:22][CH2:23][Cl:24].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[Cl:24][CH2:23][CH2:22][O:21][CH2:20][C:3]1([C:1]#[N:2])[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])[CH2:5][CH2:4]1

参加物

5

反応物 3

HCID 2733832Lithium HexamethyldisilazideHCID 102908101-chloro-2-(chloromethoxy)ethaneHCID 22028286Benzyl 4-cyanopiperidine-1-carboxylate

生成物 1

HCID 67271943HCID 67271943、化合物収率 86.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of benzyl 4-cyanopiperidine-1-carboxylate (10.0 g, 41 mmol) and 2-chloroethyl chloromethyl ether (6.3 mL, 49.2 mmol) in THF (80 mL) was cooled to −78° C. To this solution was added drop wise LiHMDS (50 mL, 50 mmol, 1N in THF) and the resulting mixture was gradually warmed to room temp over 5 h. The reaction was quenched with water and the organic phase was washed with brine, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (1:1 EtOAc/hexane) to give the title compound as yellow oil (11.9 g, 86% yield). 1H NMR (300 MHz, CDCl3) δ: 7.33-7.31 (5H, m), 5.10 (2H, d, J=5.9 Hz), 4.21 (2H, bs), 3.79-3.76 (2H, m), 3.63-3.60 (2H, m), 3.52-3.51 (2H, m), 3.09 (2H, bs), 1.96-1.92 (2H, m), 1.55-1.51 (2H, m).

後処理

  1. customThe reaction was quenched with water
  2. washthe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (1:1 EtOAc/hexane)

出典と根拠

ORDレコード
ord-9af7343dc09e4601873c16461fc5d8db
出典データセット
uspto-grants-2011_03
特許番号
US07897593B2

関連ノート

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