Benzyl Bromide → Tert-butyl 1-benzyl-2-oxo-8-(2-oxopyrrolidin-1-yl)-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

HRID 1887723Notes

Reaction equation

HRID 1887723 reaction equation
BrCC1C=CSC=1.[CH2:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[O:16]=[C:17]1[CH:26]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:25][C:24]2[C:19](=[C:20]([N:35]3[CH2:39][CH2:38][CH2:37][C:36]3=[O:40])[CH:21]=[CH:22][CH:23]=2)[NH:18]1>>[CH2:8]([N:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][C:20]=2[N:35]2[CH2:39][CH2:38][CH2:37][C:36]2=[O:40])[CH2:25][CH:26]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:31])([CH3:33])[CH3:32])[C:17]1=[O:16])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 5207033-(Bromomethyl)thiopheneHCID 59620362Tert-butyl 2-oxo-8-(2-oxopyrrolidin-1-yl)-1,2,3,4-tetrahydroquinolin-3-ylcarbamate2×

Product 1

HCID 59620395Tert-butyl 1-benzyl-2-oxo-8-(2-oxopyrrolidin-1-yl)-1,2,3,4-tetrahydroquinolin-3-ylcarbamate

Procedure

Instead of 3-bromomethylthiophene, benzylbromide (1.48 mL) was used with respect to tert-butyl 2-oxo-8-(2-oxopyrrolidin-1-yl)-1,2,3,4-tetrahydroquinolin-3-ylcarbamate (Compound B) (4.3 g), which had been produced through the same method as employed in Example 7(a), whereby the title compound (5.87 g) was yielded.

Workup

  1. customhad been produced through the same method

Sources & evidence

ORD record
ord-054576263887419c840249b881ed9859
Source dataset
uspto-grants-2013_08
Patent number
US08501772B2

Reaction notes

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