Triethylamine → HCID 58010986, compound

HRID 2062297Notes

Reaction equation

HRID 2062297 reaction equation
[NH2:1][CH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.C(N(CC)CC)C.Cl[C:24]([O:26][CH2:27][CH2:28][O:29][CH3:30])=[O:25]>C(Cl)Cl>[CH3:30][O:29][CH2:28][CH2:27][O:26][C:24](=[O:25])[NH:1][CH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 694002-Methoxyethyl chloroformateHCID 1502022tert-Butyl (3S)-3-(aminomethyl)piperidine-1-carboxylate

Product 1

HCID 58010986HCID 58010986, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 3-(aminomethyl)piperidine-1-carboxylate (500 mg, 2.33 mmol) in CH2Cl2 at −10° C. was added triethylamine (650 μL, 4.66 mmol) followed by the dropwise addition of 2-methoxyethyl chloroformate (325 μL, 2.79 mmol). The reaction was warmed to room temperature and quenched with water. The aqueous layer was extracted with CH2Cl2, and the combined extracts were dried over MgSO4, filtered, and evaporated. Purification via silica gel chromatography using 0 to 10% EtOAc in CH2Cl2 afforded 2-methoxyethyl((S)-1-(tert-butoxycarbonyl)piperidin-3-yl)methylcarbamate (496 mg, 67%). LC/MS: m/z 317.3 (M+H)+ at 2.56 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customquenched with water
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. dry with materialthe combined extracts were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customPurification via silica gel chromatography

Sources & evidence

ORD record
ord-e692f903f1644eb6a4506af81acef8cd
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

Loading…