[1-({[tert-Butyl(dimethyl)silyl]oxy}methyl)cyclopropyl]methyl methanesulfonate → tert-Butyl (3S)-3-{[(6-bromo-2-{[1-({[tert-butyl(dimethyl)silyl]oxy}methyl)-cyclopropyl]methyl}-1-oxo-1,2-dihydroisoquinolin-4-yl)sulfanyl]methyl}piperidine-1-carboxylate

HRID 906465Notes

Reaction equation

HRID 906465 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH:6]=[C:5]2[S:13][CH2:14][C@H:15]1[CH2:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]1.CS(O[CH2:33][C:34]1([CH2:37][O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])[CH2:36][CH2:35]1)(=O)=O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:33][C:34]1([CH2:37][O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])[CH2:35][CH2:36]1)[CH:6]=[C:5]2[S:13][CH2:14][C@H:15]1[CH2:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]1

Participants

3

Reactant 2

HCID 59000927[1-({[tert-Butyl(dimethyl)silyl]oxy}methyl)cyclopropyl]methyl methanesulfonateHCID 86640976tert-Butyl (3S)-3-{[(6-bromo-1-oxo-1,2-dihydroisoquinolin-4-yl)sulfanyl]methyl}-piperidine-1-carboxylate

Product 1

HCID 86640975tert-Butyl (3S)-3-{[(6-bromo-2-{[1-({[tert-butyl(dimethyl)silyl]oxy}methyl)-cyclopropyl]methyl}-1-oxo-1,2-dihydroisoquinolin-4-yl)sulfanyl]methyl}piperidine-1-carboxylateYield 40.3%

Procedure

tert-Butyl (3S)-3-{[(6-bromo-1-oxo-1,2-dihydroisoquinolin-4-yl)sulfanyl]methyl}-piperidine-1-carboxylate (Example 63c, 190 mg) was reacted with [1-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopropyl]methyl methanesulfonate (136 mg) by the method of Example 58c to afford the subtitle compound (110 mg) as a colourless oil.

Sources & evidence

ORD record
ord-60c938acf22f409792899d85c63eaf51
Source dataset
uspto-grants-2011_09
Patent number
US08012980B2

Reaction notes

Loading…