Methanol → Methyl 2-oxospiro[indoline-3,4'-piperidine]-5-carboxylate hydrochloride

HRID 390165ノート

反応式

HRID 390165 の反応式
C(OC([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:22]([OH:24])=[O:23])[CH:20]=3)[NH:15][C:14]2=[O:25])[CH2:10][CH2:9]1)=O)(C)(C)C.O=S(Cl)[Cl:28].[CH3:30]O>>[ClH:28].[O:25]=[C:14]1[C:11]2([CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:22]([O:24][CH3:30])=[O:23])[CH:20]=2)[NH:15]1

参加物

4

反応物 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 497601931'-(Tert-butoxycarbonyl)-2-oxospiro[indoline-3,4'-piperidine]-5-carboxylic acid

生成物 1

HCID 67223037Methyl 2-oxospiro[indoline-3,4'-piperidine]-5-carboxylate hydrochloride収率 81%

実験手順

To a solution of 1′-(tert-butoxycarbonyl)-2-oxospiro[indoline-3,4′-piperidine]-5-carboxylic acid (2 g, 6.0 mmol) in methanol (30 mL) was added dropwise SOCl2 (5 mL) at 0° C. Then the reaction mixture was stirred overnight at rt. The reaction mixture was concentrated to give methyl 2-oxospiro[indoline-3,4′-piperidine]-5-carboxylate hydrochloride (1.4 g, 81%), which was used for the next step without purification. 1H NMR (CD3OD): 2.00 (m, 2H), 2.20 (m, 2H), 3.281 (m, 1H), 3.39 (m, 2H), 3.61 (m, 2H), 3.85 (m, 2H), 3.88 (m, 2H), 7.00 (m, 1H), 7.98 (m, 2H).

後処理

  1. concentrationThe reaction mixture was concentrated

出典と根拠

ORDレコード
ord-332cae25456343b58a77f49bc41abff3
出典データセット
uspto-grants-2013_02
特許番号
US08383629B2

反応ノート

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