HCID 59371519, compound → HCID 59371316, compound

HRID 2095365Notes

Reaction equation

HRID 2095365 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[C:16]([CH2:20][CH2:21][C:22]2[CH:23]=[C:24]([CH2:28][N:29]=[N+]=[N-])[CH:25]=[CH:26][CH:27]=2)[CH:17]=[N:18][CH:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.O=[Pt]=O>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[C:16]([CH2:20][CH2:21][C:22]2[CH:23]=[C:24]([CH2:28][NH2:29])[CH:25]=[CH:26][CH:27]=2)[CH:17]=[N:18][CH:19]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 59371519HCID 59371519, compound

Product 1

HCID 59371316HCID 59371316, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

3-[2-[5-[[1-(tert-Butoxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]ethyl]phenylmethyl azide is dissolved in ethanol, and a catalytic amount of PtO2 is added. The reaction flask is attached to a H2 balloon by way of a three-way stopcock, and the atmosphere is exchanged. The mixture is stirred at room temperature. The reaction is followed by TLC and terminated by replacing the atmosphere with N2 when the starting material has disappeared. The catalyst is removed by centrifugation or filtration over a filter membrane. The solution is evaporated and the residue used directly in the following step. If desired, the product can be purified by CC on silica gel eluting with CH2Cl2/methanol/Et3N or CH2Cl2/methanol/conc. aqueous NH3, or on deactivated basic alumina with CH2Cl2/methanol.

Workup

  1. customterminated
  2. customThe catalyst is removed by centrifugation or filtration over a filter membrane
  3. customThe solution is evaporated
  4. customthe product can be purified by CC on silica gel eluting with CH2Cl2/methanol/Et3N or CH2Cl2/methanol/conc

Sources & evidence

ORD record
ord-764bd7fb4b4f430298b12556754456bf
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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