(RS)-2-(2-Benzofuranylcarbonyl)-1-(tert-butyloxycarbonyl)piperidine → HCID 23146318, compound

HRID 2077276Notes

Reaction equation

HRID 2077276 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][N:13]1C(OC(C)(C)C)=O)=[O:11]>FC(F)(F)C(O)=O.ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][NH:13]1)=[O:11]

Participants

4

Reactant 1

HCID 23146395(RS)-2-(2-Benzofuranylcarbonyl)-1-(tert-butyloxycarbonyl)piperidine

Product 1

HCID 23146318HCID 23146318, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (RS)-2-(2-benzofuranylcarbonyl)-1-(tert-butyloxycarbonyl)piperidine, D2 (0.86 g, 2.61 mmol) in trifluoroacetic acid (5 ml) and dichloromethane (20 ml) was warmed at 35° C. for 0.5 h. The reaction mixture was evaporated in vacuo and the residue partitioned between dichloromethane (30 ml) and 1N sodium hydroxide (30 ml). The aqueous layer was extracted with dichloromethane (30 ml) and the combined organic layers dried (Na2SO4) and evaporated in vacuo to afford the title compound as a pale yellow gum (0.59 g, 99%).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe residue partitioned between dichloromethane (30 ml) and 1N sodium hydroxide (30 ml)
  3. extractionThe aqueous layer was extracted with dichloromethane (30 ml)
  4. dry with materialthe combined organic layers dried (Na2SO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-1e31b1364b58480dbcaaec13d3e82f4f
Source dataset
uspto-grants-2011_04
Patent number
US07928124B2

Reaction notes

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