Succinic anhydride → 4-(1'-(2-Adamantylcarbamoyl)spiro[indoline-3,4'-piperidine]-1-yl)-4-oxobutanoic acid

HRID 1424627Notes

Reaction equation

HRID 1424627 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([N:14]1[CH2:19][CH2:18][C:17]3([C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[NH:21][CH2:20]3)[CH2:16][CH2:15]1)=[O:13])[CH2:8]2.[C:28]1(=[O:34])[O:33][C:31](=[O:32])[CH2:30][CH2:29]1>C(Cl)Cl>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([N:14]1[CH2:15][CH2:16][C:17]3([C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]([C:28](=[O:34])[CH2:29][CH2:30][C:31]([OH:33])=[O:32])[CH2:20]3)[CH2:18][CH2:19]1)=[O:13])[CH2:8]2

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 25067083N-(2-adamantyl)spiro[indoline-3,4'-piperidine]-1'-carboxamide

Product 1

HCID 581372924-(1'-(2-Adamantylcarbamoyl)spiro[indoline-3,4'-piperidine]-1-yl)-4-oxobutanoic acidYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2-adamantyl)spiro[indoline-3,4′-piperidine]-1′-carboxamide (20 mg, 0.06 mmol) and succinic anhydride (12 mg, 0.12 mmol) in CH2Cl2 (5 mL) was added TEA. After stirred for 2 h at rt the solvent was removed to give 4-(1′-(2-adamantylcarbamoyl)spiro[indoline-3,4′-piperidine]-1-yl)-4-oxobutanoic acid (20 mg, 74%). LC-MS Method 5 tR=3.6 min, m/z=953.1; 1H NMR (CD3OD) δ=1.69 (d, 2H), 1.75 (d, 2H), 1.80-1.99 (m, 11H), 2.00-2.10 (m, 5H), 2.20 (s, 2H), 2.60-2.70 (m, 2H), 2.80-2.90 (m, 2H), 3.06-3.18 (m, 2H), 3.93 (s, 1H), 4.10-4.19 (m, 2H), 4.20 (s, 2H), 5.90 (d, 1H), 7.10 (m, 1H), 7.19-7.28 (m, 2H), 8.16 (d, 1H).

Workup

  1. customwas removed

Sources & evidence

ORD record
ord-adaad5e05b6f47f481f983d13a3aad58
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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