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

HRID 723474Notes

Reaction equation

HRID 723474 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([CH2:25][CH3:26])CC)C>C(Cl)Cl>[CH2:11]([O:10][C:8]([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:9])[C:26]1[CH:25]=[CH:4][CH:3]=[CH:2][CH:7]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 58745614(3R,4R)-1-tert-butyl 3-ethyl 4-aminopiperidine-1,3-dicarboxylate

Product 1

HCID 66952821(3R,4R)-1-tert-butyl 3-ethyl 4-(benzyloxycarbonyl)piperidine-1,3-dicarboxylateYield 188.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 252E (180 mg, 0.66 mmol) in CH2Cl2 (5 mL) was treated with benzyloxychloroformate (0.1 mL, 0.73 mmol) and triethylamine (0.12 mL, 0.86 mmol). The reaction was stirred at room temperature for 18 hours, diluted with CH2Cl2 (10 mL) and washed with water (2×10 mL), 0.1 N HCl (2×10 mL), saturated aqueous NaHCO3 (2×10 mL) and brine (1×10 mL). The organic layer was dried (Na2SO4), filtered and concentrated to give 243 mg (yield: 91%) of Compound 254A as an oil.

Workup

  1. washwashed with water (2×10 mL), 0.1 N HCl (2×10 mL), saturated aqueous NaHCO3 (2×10 mL) and brine (1×10 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dc360af6e8cf437ea52755a44f1fd2bc
Source dataset
uspto-grants-2006_11
Patent number
US07141571B2

Reaction notes

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