Piperidine → (R)-1-((5-azido-5,6,7,8-tetrahydronaphthalen-2-yl)methyl)piperidine

HRID 1431992Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1431992
[N:1]([C@@H:4]1[CH2:13][CH2:12][CH2:11][C:10]2[CH:9]=[C:8]([CH:14]=O)[CH:7]=[CH:6][C:5]1=2)=[N+:2]=[N-:3].[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(OC)(OC)OC.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CC(O)=O.C(Cl)Cl>[N:1]([C@@H:4]1[CH2:13][CH2:12][CH2:11][C:10]2[CH:9]=[C:8]([CH2:14][N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH:7]=[CH:6][C:5]1=2)=[N+:2]=[N-:3]

Komponenten

7

Edukt 4

HCID 8082PiperidineHCID 9005Trimethyl orthoformateHCID 5049666Sodium triacetoxyborohydrideHCID 59771822(R)-5-azido-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde

Produkt 1

HCID 86604857(R)-1-((5-azido-5,6,7,8-tetrahydronaphthalen-2-yl)methyl)piperidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a 100 mL flame dry round bottom flask was added (R)-5-azido-5,6,7,8-tetrahydro-naphthalene-2-carbaldehyde (200 mg, 0.99 mmol), piperidine (0.5 mL, 5 mmol), dry DCM (10 mL), HOAc (1 drop), and CH(OMe)3. The resulting mixture was stirred under N2 for 3 h at RT. Then, NaBH(OAc)3 (632 mg, 2.98 mmol) was added and stirred for 20 h. The reaction mixture was quenched with 5% NaHCO3 and concentrated in vacuo. The residue was partitioned between EtOAc and H2O. The organic layer was washed with H2O, brine, dried over MgSO4 and concentrated. The residue was purified by SiO2 (95% DCM:5% MeOH) to afford the title compound. MS (m/z): 271.2 (M+H) (Calc'd. for C16H22N4:270.37).

Aufarbeitung

  1. temperatureTo a 100 mL flame
  2. customdry round bottom flask
  3. stirringstirred for 20 h
  4. customThe reaction mixture was quenched with 5% NaHCO3
  5. concentrationconcentrated in vacuo
  6. customThe residue was partitioned between EtOAc and H2O
  7. washThe organic layer was washed with H2O, brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customThe residue was purified by SiO2 (95% DCM:5% MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-e852cfd629a842d19b4d315d068b2038
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612060B2

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