tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate → tert-Butyl 8-[6-bromo-3-(cyclopropanecarbonyl)quinolin-4-yl]-2,8-diazaspiro[4,5]decane-2-carboxylate

HRID 2271573Notes

Reaction equation

HRID 2271573 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([CH:14]1[CH2:16][CH2:15]1)=[O:13])=[C:5]2Cl.[CH2:18]1[C:22]2([CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH2:21][CH2:20][N:19]1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([CH:14]1[CH2:16][CH2:15]1)=[O:13])=[C:5]2[N:25]1[CH2:26][CH2:27][C:22]2([CH2:18][N:19]([C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])[CH2:20][CH2:21]2)[CH2:23][CH2:24]1

Participants

3

Reactant 2

HCID 34178604tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylateHCID 66715111(6-Bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone

Product 1

HCID 66715811tert-Butyl 8-[6-bromo-3-(cyclopropanecarbonyl)quinolin-4-yl]-2,8-diazaspiro[4,5]decane-2-carboxylateYield 73%

Procedure

Following general procedure B, (6-bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone (200 mg, 0.640 mmol) was reacted with tert-butyl 2,8-diazaspiro[4,5]decane-2-carboxylate (169 mg, 0.704 mmol) to afford the desired product (240 mg, 73%) as a yellow foam: ESI MS m/z 514 [C26H32BrN3O3+H]+.

Sources & evidence

ORD record
ord-67591f95c68e46609f7ff19ee7705a1b
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

Loading…