Acetyl chloride → tert-Butyl 1-acetyl-5-chlorospiro[indoline-3,4'-piperidine]-1'-carboxylate

HRID 706351ノート

反応式

HRID 706351 の反応式
[C:1](Cl)(=[O:3])[CH3:2].[C:5]([O:9][C:10]([N:12]1[CH2:17][CH2:16][C:15]2([C:25]3[C:20](=[CH:21][CH:22]=[C:23]([Cl:26])[CH:24]=3)[NH:19][CH2:18]2)[CH2:14][CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].C(N(CC)CC)C>ClCCl>[C:5]([O:9][C:10]([N:12]1[CH2:13][CH2:14][C:15]2([C:25]3[C:20](=[CH:21][CH:22]=[C:23]([Cl:26])[CH:24]=3)[N:19]([C:1](=[O:3])[CH3:2])[CH2:18]2)[CH2:16][CH2:17]1)=[O:11])([CH3:8])([CH3:6])[CH3:7]

参加物

5

反応物 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 46835581Tert-butyl 5-chlorospiro[indoline-3,4'-piperidine]-1'-carboxylate

生成物 1

HCID 58046557tert-Butyl 1-acetyl-5-chlorospiro[indoline-3,4'-piperidine]-1'-carboxylate収率 87%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Acetyl chloride (2.8 ml) was added dropwise to a stirred solution of 5-chlorospiro[indoline-3,4′-piperidine]-1′-carboxylic acid tert-butyl ester (9.8 g) and triethylamine (15 ml) in anhydrous dichloromethane (400 ml) under an atmosphere of nitrogen. The reaction was stirred for 1 h and was then quenched with saturated sodium bicarbonate solution (200 ml). The organic layer was dried over anhydrous sodium sulphate and concentrated in vacuo to yield 9.8 g (87%) of the desired amide as an off-white solid. M.p. 64-66° C. 1H NMR (400 MHz, CDCl3) δ 6:1 mixture of rotamers. Major rotamer 1.5 (9H, s), 1.70 (m, 2H), 1.85 (m, 2H), 2.25 (s, 3H), 2.85 (m, 2H), 3.90 (s, 2H), 4.2 (m, 2H), 6.97 (d, J=1 Hz, 1H), 7.20 (dd, J=7 & 1 Hz, 1H), 8.15 (d, J=7 Hz, 1H). Minor rotamer 1.5 (9H, s), 1.70 (m, 2H), 1.85 (m, 2H), 2.45 (s, 3H), 2.85 (m, 2H), 4.05 (s, 2H), 4.2 (m, 2H), 7.2 (d, J=1 Hz, 1H), 7.25 (dd, J=7 & 1 Hz, 1H), 7.48 (d, J=7 Hz, 1H).

後処理

  1. customwas then quenched with saturated sodium bicarbonate solution (200 ml)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  3. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-716af16337de4463ae5428fd85fedf81
出典データセット
uspto-grants-2015_11
特許番号
US09174987B2

反応ノート

読み込み中…