Dibutyltin oxide → HCID 178495051, compound

HRID 1184150Notes

Reaction equation

HRID 1184150 reaction equation
[C:1]([C@@H:3]1[CH2:8][C@H:7]([N:9]([C:14]([C:16]2[N:20]([CH2:21][CH2:22][CH2:23][CH2:24][O:25][CH3:26])[C:19]3[CH:27]=[CH:28][CH:29]=[CH:30][C:18]=3[N:17]=2)=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])[CH2:6][N:5]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:4]1)#[N:2].[N:38]([Si](C)(C)C)=[N+:39]=[N-:40].C([Sn](CCCC)=O)CCC>O1CCCC1>[CH3:26][O:25][CH2:24][CH2:23][CH2:22][CH2:21][N:20]1[C:19]2[CH:27]=[CH:28][CH:29]=[CH:30][C:18]=2[N:17]=[C:16]1[C:14]([N:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[C@H:7]1[CH2:8][C@@H:3]([C:1]2[NH:40][N:39]=[N:38][N:2]=2)[CH2:4][N:5]([C:31]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[O:32])[CH2:6]1)=[O:15]

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 58355698tert-butyl (3R,5S)-3-cyano-5-{{{1-(4-methoxybutyl)-1H-benzimidazol-2-yl}carbonyl}(2-methylpropyl)amino}piperidine-1-carboxylate

Product 1

HCID 178495051HCID 178495051, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl (3R,5S)-3-cyano-5-{{{1-(4-methoxybutyl)-1H-benzimidazol-2-yl}carbonyl}(2-methylpropyl)amino}piperidine-1-carboxylate (320 mg) was dissolved in tetrahydrofuran (20 ml), azido(trimethyl)silane (1.5 ml) and dibutyl(oxo)stannane (100 mg) were added, and the mixture was heated under reflux with stirring for 43 hr. The reaction mixture was concentrated under reduced pressure, and the residue was subjected to silica gel chromatography, and a fraction eluted with ethyl acetate-ethyl acetate-methanol (8:2) was concentrated under reduced pressure to give the object product (304 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. washa fraction eluted with ethyl acetate-ethyl acetate-methanol (8:2)
  5. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-27aa51523b814d82b7c423388d20d2c9
Source dataset
uspto-grants-2014_03
Patent number
US08664380B2

Reaction notes

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