Benzyl chloroformate → Benzyl [(2S,3S)-2-phenylpiperidin-3-yl]carbamate

HRID 1065974

Reaktionsgleichung

Reaktionsgleichung von HRID 1065974
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][NH:4][C@H:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH2:18]([O:17][C:15]([NH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][NH:4][C@H:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:16])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 9812908(2S,3S)-2-phenylpiperidin-3-amine

Produkt 1

HCID 57054031Benzyl [(2S,3S)-2-phenylpiperidin-3-yl]carbamateAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of (2S,3S)-(−)-3-amino-2-phenylpiperidine (152 mg, 0.86 mmole) (L-tartaric acid salt, [a]D=−57.1 (EtOH, c=0.1138)) in methylene chloride (10 mL) at room temperature was added benzyl chloroformate (0.123 mL, 0.86 mmole) and diisopropylethylamine (0.45 mL, 2.58 mmole). The reaction was stirred for 16 hours and was then diluted with methylene chloride and quenched by addition of water. The mixture was separated and the aqueous was reextracted with 2 additional aliquots of methylene chloride. The organic layers were successively washed with a portion of brine, dried over sodium sulfate, combined and evaporated. The residue was purified by flash chromatography (5% methanol in methylene chloride) to afford 214 mg (80%) of the title compound. NMR (CDCl3): δ 1.55 (br, d, J=9 Hz, 1 H), 1.6-1.9 (m, 2 H), 2.02 (br. d, J=9 Hz, 1 H), 2.79 (dd, J=9 and 10 Hz, 1 H), 3.22 (dd, J=1 and 10 Hz, 1 H), 3.91 (br. s, 1 H), 4.01 (dd, J=1 and 8 Hz, 1 H), 4.89 (s, 2 H), 5.65 and 5.88 (2 br. s, 1 H), 7.1-7.4 (m, 10 H).

Aufarbeitung

  1. customquenched by addition of water
  2. customThe mixture was separated
  3. washThe organic layers were successively washed with a portion of brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue was purified by flash chromatography (5% methanol in methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-a1291f80efb845d6bd83883244473bf6
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06241964B1

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