Trifluoroacetic acid → 1-(5-Chlorospiro[indoline-3,4'-piperidin]-1-yl)ethanone

HRID 706352ノート

反応式

HRID 706352 の反応式
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][C:18]2([C:28]3[C:23](=[CH:24][CH:25]=[C:26]([Cl:29])[CH:27]=3)[N:22]([C:30](=[O:32])[CH3:31])[CH2:21]2)[CH2:17][CH2:16]1)=O)(C)(C)C.CO.ClCCl.C(N(CC)CC)C>ClCCl>[C:30]([N:22]1[C:23]2[C:28](=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[C:18]2([CH2:19][CH2:20][NH:15][CH2:16][CH2:17]2)[CH2:21]1)(=[O:32])[CH3:31]

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 21913430dichloromethane MeOH Et3NHCID 58046557tert-Butyl 1-acetyl-5-chlorospiro[indoline-3,4'-piperidine]-1'-carboxylate

生成物 1

HCID 573199971-(5-Chlorospiro[indoline-3,4'-piperidin]-1-yl)ethanone収率 96.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Trifluoroacetic acid (25 ml) was added to a stirred solution of 1-acetyl-5-chlorospiro[indoline-3,4′-piperidine]-1′-carboxylic acid tert-butyl ester (8 g) in anhydrous dichloromethane (250 ml) under an atmosphere of nitrogen. The reaction was left as such for 3 h. The reaction was washed with saturated bicarbonate solution (200 ml) and dried over sodium sulphate and concentrated in vacuo to yield an off white solid. Flash chromatography [SiO2: methanol-dichloromethane-triethylamine (90:5:5)] yielded 5.6 g (61%) of the desired 1-Acetyl-5-chlorospiro[indoline-3,4′-piperidine]. 1H NMR (400 MHz, CDCl3) δ 6:1 mixture of rotamers. Major rotamer 1.70 (m, 2H), 1.80 (m, 2H), 2.27 (s, 3H), 2.75 (t, J=12 Hz, 2H), 3.15 (m, 2H), 3.90 (s, 2H), 7.12 (d, J=1 Hz, 1H), 7.18 (dd, J=7 & 1 Hz, 1H), 8.15 (d, J=7 Hz, 1H). Minor rotamer (partial data) 2.44 (s, 3H), 2.86 (m, 2H), 3.10 (m, 2H), 4.05 (s, 2H). MS (ES+) 265/267 (M+H+).

後処理

  1. washThe reaction was washed with saturated bicarbonate solution (200 ml)
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated in vacuo
  4. customto yield an off white solid

出典と根拠

ORDレコード
ord-85da83f406c64a469634755ac4e37f9e
出典データセット
uspto-grants-2015_11
特許番号
US09174987B2

反応ノート

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