Dichloromethane → O2-benzyl O9-tert-butyl 2,9-diazaspiro[5.5]undecane-2,9-dicarboxylate

HRID 2284871Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2284871
Cl.[CH2:2]1[C:7]2([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[CH2:6][NH:5][CH2:4][CH2:3]1.ClCCl.C(N(CC)CC)C.Cl[C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32]>O>[CH2:2]1[C:7]2([CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:12]2)[CH2:6][N:5]([C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:32])[CH2:4][CH2:3]1

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 71464197Tert-butyl 2,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride

Produkt 1

HCID 118049948O2-benzyl O9-tert-butyl 2,9-diazaspiro[5.5]undecane-2,9-dicarboxylateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a 20 L temperature controlled reactor charge tert-butyl 4,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride (2.06 moles; 600.00 g) followed by dichloromethane (6.00 L), then triethylamine (4.33 moles; 604 mL) is added. Set the jacket of the reactor to 0° C. When the temperature of the reaction mixture reaches 5° C., add benzyl chloroformate (2.10 moles; 311 mL) over about 20 minutes keeping the internal temperature below 20° C. When the addition is complete, warm the jacket to room temperature and stir the mixture overnight. Pour the reaction mixture into water (4 L) and separate the mixture. Concentrate the organics under reduced pressure to give the title compound (838 g; assumed 95.65% purity and 100% yield for the purposes of calculation in the next reaction) mass spectrum (m/z): 411.2 (M+23).

Aufarbeitung

  1. customto 0° C
  2. customreaches 5° C.
  3. customthe internal temperature below 20° C
  4. additionWhen the addition
  5. customseparate the mixture
  6. concentrationConcentrate the organics under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9799e32c2a3048f4804da459b1d876e0
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09145437B2

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