Sodium Hydroxide → Tert-butyl[3-(7-benzyl-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)propyl]carbamate

HRID 2078442Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2078442
Cl.Cl.[CH2:3]([N:10]1[CH2:17][CH:16]2[O:18][CH:12]([CH2:13][NH:14][CH2:15]2)[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+].CC1C=C(C)C=C(C)C=1S(O[CH2:34][CH2:35][CH2:36][NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])(=O)=O>C1(C)C=CC=CC=1>[C:41]([O:40][C:38](=[O:39])[NH:37][CH2:36][CH2:35][CH2:34][N:14]1[CH2:15][CH:16]2[O:18][CH:12]([CH2:11][N:10]([CH2:3][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:17]2)[CH2:13]1)([CH3:44])([CH3:43])[CH3:42]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 185403703-(Phenylmethyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane, hydrochloride (1:2)HCID 866280503-(tert-Butyloxycarbonylamino)propyl 2,4,6-trimethylbenzenesulfonate

Produkt 1

HCID 15980224Tert-butyl[3-(7-benzyl-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)propyl]carbamateAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To 3-benzyl-9-oxa-3,7-diazabicyclo[3.3.1]nonane dihydrochloride (25.08 g, 86.12 mmol; see Preparation O above) was added 2.5 M sodium hydroxide (115 mL). 3-(tert-Butyloxycarbonylamino)propyl 2,4,6-trimethylbenzenesulfonate (32.35 g, 90.50 mmol; see Preparation L above) and toluene (65 mL) were then added and the reaction mixture heated at 65° C. for 12 hours. The phases were separated at 65° C. and the lower (aqueous) layer discarded. The organic phase was re-heated to 65° C. and then extracted with 10% w/w aqueous citric acid (125 mL). The phases were separated and the upper (organic) phase discarded. To the aqueous citric acid phase was added isopropyl acetate (150 mL) and 5 M sodium hydroxide (75 mL). The resulting mixture was stirred at room temperature for 15 minutes. The phases were separated and the lower (aqueous) phase discarded. The resulting organic phase was dried (MgSO4), filtered and the solvent removed in vacuo to give the title compound as a colourless oil (29.13 g, 77.60 mmol, 90%).

Aufarbeitung

  1. customThe phases were separated at 65° C.
  2. temperatureThe organic phase was re-heated to 65° C.
  3. extractionextracted with 10% w/w aqueous citric acid (125 mL)
  4. customThe phases were separated
  5. additionTo the aqueous citric acid phase was added isopropyl acetate (150 mL) and 5 M sodium hydroxide (75 mL)
  6. customThe phases were separated
  7. dry with materialThe resulting organic phase was dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-25ad5fa932a4471a9815abb80ea50374
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07928225B2

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