Dibutyltin oxide → HCID 178525128, compound

HRID 216264Notes

Reaction equation

HRID 216264 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]#[N:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Sn](=O)CCCC)CCC.C[Si]([N:33]=[N+:34]=[N-:35])(C)C>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]2[NH:35][N:34]=[N:33][N:18]=2)[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378Azidotrimethylsilane2×HCID 44828669Benzyl 3-cyanopiperidine-1-carboxylate

Product 1

HCID 178525128HCID 178525128, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

To a mixture of 3-cyano-piperidine-1-carboxylic acid benzyl ester (1 g, 4.1 mmol), and dibutyltinoxide (153 mg, 0.6 mmol) in toluene (8 mL) is added trimethylsilylazide (1.1 mL, 8.2 mmol) at room temperature. After the mixture is heated at 95° C. for 15 h, more trimethylsilylazide (2 mL, 15 mmol) is added and the stirring is continued for 6 h at 95° C. The mixture is concentrated, and the resulting solid is triturated with heptane (30 mL) and filtered to afford 3-(1H-tetrazol-5-yl)-piperidine-1-carboxylic acid benzyl ester (1 g). LCMS: RT=2.31 minutes, MS: 288 (M+H).

Workup

  1. concentrationThe mixture is concentrated
  2. customthe resulting solid is triturated with heptane (30 mL)
  3. filtrationfiltered

Sources & evidence

ORD record
ord-b08746de43ee4d22b143e094f79e51de
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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