Triethylamine → (3S,4R)-1-tert-butyl 3-ethyl 4-(allyloxycarbonyl)piperidine-1,3-dicarboxylate

HRID 723479Notes

Reaction equation

HRID 723479 reaction equation
N[C@@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C@@H:3]1[C:15]([O:17][CH2:18][CH3:19])=[O:16].C(N(CC)CC)C.[CH2:27]([O:30][C:31](Cl)=[O:32])[CH:28]=[CH2:29]>C(Cl)Cl>[CH2:27]([O:30][C:31]([C@@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C@H:3]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:32])[CH:28]=[CH2:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18052Allyl chloroformateHCID 587454941-tert-butyl 3-ethyl (3S,4R)-4-aminopiperidine-1,3-dicarboxylate

Product 1

HCID 66952501(3S,4R)-1-tert-butyl 3-ethyl 4-(allyloxycarbonyl)piperidine-1,3-dicarboxylateYield 60.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 259A (900 mg, 3.3 mmol) in CH2Cl2 (20 mL) was treated with triethylamine (0.64 mL, 4.62 mmol) and allylchloroformate (0.35 mL, 3.96 mmol) at room temperature. The mixture was stirred for four hours, then washed with 0.1 N HCl (2×10 mL), 1N NaOH (2×10 mL) and brine (10 mL). The organic layer was dried (Na2SO4), filtered and concentrated in vacuo to give 680 mg (yield: 58%) of Compound 259B as an oil.

Workup

  1. washwashed with 0.1 N HCl (2×10 mL), 1N NaOH (2×10 mL) and brine (10 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d342c7232c0e4ae19ccef030cad66712
Source dataset
uspto-grants-2006_11
Patent number
US07141571B2

Reaction notes

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