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

HRID 2070125Notes

Reaction equation

HRID 2070125 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-98ee0451118848a486b0b312e0630a04
Source dataset
uspto-grants-2012_10
Patent number
US08299255B2

Reaction notes

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