Dibutyltin oxide → HCID 178494887, compound

HRID 1798481Notes

Reaction equation

[C:1]([C:3]1[CH:60]=[CH:59][C:6]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:51]=[C:52]([CH2:54][CH2:55][CH2:56][O:57][CH3:58])[CH:53]=2)[CH2:12][N:13]([CH:48]2[CH2:50][CH2:49]2)[C:14]([C@@H:16]2[C@@H:21]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][O:31][C:32]4[C:37]([Cl:38])=[CH:36][C:35]([CH3:39])=[CH:34][C:33]=4[Cl:40])=[CH:24][CH:23]=3)[CH2:20][CH2:19][N:18]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:17]2)=[O:15])=[CH:5][CH:4]=1)#[N:2].[N:61]([Si](C)(C)C)=[N+:62]=[N-:63].C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[CH:48]1([N:13]([CH2:12][C:11]2[CH:10]=[C:9]([O:8][CH2:7][C:6]3[CH:59]=[CH:60][C:3]([C:1]4[NH:63][N:62]=[N:61][N:2]=4)=[CH:4][CH:5]=3)[CH:53]=[C:52]([CH2:54][CH2:55][CH2:56][O:57][CH3:58])[CH:51]=2)[C:14]([C@@H:16]2[C@@H:21]([C:22]3[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH2:30][O:31][C:32]4[C:33]([Cl:40])=[CH:34][C:35]([CH3:39])=[CH:36][C:37]=4[Cl:38])=[CH:26][CH:27]=3)[CH2:20][CH2:19][N:18]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:17]2)=[O:15])[CH2:50][CH2:49]1

Participants

Conditions

Temperature: 105 °C

Procedure

To a solution of tert-butyl (3R,4S)-3-([[3-[(4-cyanobenzyl)oxy]-5-(3-methoxy-propyl)benzyl](cyclopropyl)amino]carbonyl}-4-{4-[2-(2,6-dichloro-4-methylphen-oxy)ethoxy]phenyl}piperidine-1-carboxylate (1 eq.) from the previous step in toluene (0.04 M) was added azido(trimethyl)silane (3 eq.) and dibutyltin oxide (0.25 eq.). The reaction was heated to 105° C. and stirred for 16 h. The volatiles were removed in vacuo and the crude product was purified by flash column chromatography (SiO2, 95.9:3.9:0.2 (v/v/v) DCM/MeOH/AcOH) to afford the title compound as an oil.

Workup

customThe volatiles were removed in vacuo
customthe crude product was purified by flash column chromatography (SiO2, 95.9:3.9:0.2 (v/v/v) DCM/MeOH/AcOH)

Sources & evidence

ORD record: ord-11121ada6421448c9e09c16dbd82627e
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343968B2

Reaction notes

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