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

HRID 706351Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 706351
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-716af16337de4463ae5428fd85fedf81
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174987B2

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