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

HRID 390165Notes

Reaction equation

HRID 390165 reaction equation
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

Participants

4

Reactant 3

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

Product 1

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

Procedure

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).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-332cae25456343b58a77f49bc41abff3
Source dataset
uspto-grants-2013_02
Patent number
US08383629B2

Reaction notes

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