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Benzylamine → (1S,2S,5R)-2-(benzylamino-methyl)-7-methyl-3-aza-bicyclo[3.3.0]-octane-3-carboxylic acid tert.-butyl ester

HRID 425797
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 425797
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O:13][C:14]([N:16]1[CH2:23][C@H:22]2[C@H:18]([CH2:19][CH:20]([CH3:24])[CH2:21]2)[C@H:17]1[CH:25]=O)=[O:15])([CH3:12])([CH3:11])[CH3:10].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.CC(=O)OCC.CCCCCCC>[C:9]([O:13][C:14]([N:16]1[CH2:23][C@H:22]2[C@H:18]([CH2:19][CH:20]([CH3:24])[CH2:21]2)[C@H:17]1[CH2:25][NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:15])([CH3:12])([CH3:10])[CH3:11]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 7504BenzylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86643542(1S,2S,5R)-2-formyl-7-methyl-3-aza-bicyclo[3.3.0]-octane-3-carboxylic acid tert.-butyl ester

Produkt 1

HCID 66703797(1S,2S,5R)-2-(benzylamino-methyl)-7-methyl-3-aza-bicyclo[3.3.0]-octane-3-carboxylic acid tert.-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 21899848Ethylacetate heptaneLösungsmittel

Versuchsvorschrift

Benzylamine (0.155 mL, 1.75 eq) was added to a solution of (1S,2S,5R)-2-formyl-7-methyl-3-aza-bicyclo[3.3.0]-octane-3-carboxylic acid tert.-butyl ester (206 mg, 1 eq) in chloroform (6 mL). After 15 min the mixture was treated with NaBH(OAc)3 (173 mg, 1 eq), and stirred for 16 h. The reaction mixture was poured into a sat. aq. NaHCO3 solution. The layers were separated and the aq. layer was extracted twice with chloroform. The combined org. extracts were washed with sat. NaHCO3 solution, dried over anh. MgSO4, filtered and concentrated in vacuo to give a crude yellow oil. FC (EA/n-heptane: 3/7 to 7/3) gave the title compound as a colourless oil

Aufarbeitung

  1. customThe layers were separated
  2. extractionthe aq. layer was extracted twice with chloroform
  3. washextracts were washed with sat. NaHCO3 solution
  4. dry with materialdried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a crude yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-10fdae76badd4ad8b5b8ceab6eb296a7
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08106215B2

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