N,N,N',N'-Tetramethylazodicarboxamide → (3S)-3-Methyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino [6,7-e]indole

HRID 2423128Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2423128
[N:1](C(N(C)C)=O)=NC(N(C)C)=O.[OH:13][C:14]1[CH:22]=[CH:21][C:20]2[N:19]([S:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH:18]=[CH:17][C:16]=2[C:15]=1[CH:32]=O.[C:34]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:39]=CC=C[CH:35]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:35][C@@H:34]1[NH:1][CH2:32][C:15]2=[C:16]3[C:20](=[CH:21][CH:22]=[C:14]2[O:13][CH2:39]1)[N:19]([S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:25])=[O:24])[CH:18]=[CH:17]3

Komponenten

6

Edukt 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 11776TriphenylphosphineHCID 5049666Sodium triacetoxyborohydrideHCID 866217145-Hydroxy-1-(phenylsulfonyl)-1H-indole-4-carbaldehyde2×

Produkt 1

HCID 25057081(3S)-3-Methyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino [6,7-e]indoleAusbeute 27,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

1,1′-Azobis(N,N-dimethylformamide) (57 mg, 0.33 mmol) was added to a solution of 5-hydroxy-1-(phenylsulfonyl)-1H-indole-4-carbaldehyde (Intermediate 10, 0.050 g, 0.16 mmol), S-(−)-2-(tert-butoxycarbonylamino)-1-propanol (58 mg, 0.33 mmol) and triphenylphosphine (87 mg, 0.33 mmol) in DCM (5 mL). The mixture was stirred at 45° C. for 2 days and the mixture was evaporated. The crude material was purified by flash chromatography using 1% to 2.5% MeOH in DCM. This boc-protected intermediate was dissolved in DCM (3 mL) and TFA (1 mL) was added. The mixture was stirred for 1 hour and evaporated. The residue was dissolved in THF (3 mL) and sodium triacetoxyborohydride (30.0 mg, 0.141 mmol) was added all in one portion. The reaction mixture was stirred for 20 minutes and evaporated. The crude product was purified by flash chromatography on silica gel using MeOH:DCM:NEt3 (5:94:1) as the eluent to give a light yellow solid (15 mg) of the title compound. MS m/z 343 [M+H]+.

Aufarbeitung

  1. customthe mixture was evaporated
  2. customThe crude material was purified by flash chromatography
  3. dissolutionwas dissolved in DCM (3 mL)
  4. additionTFA (1 mL) was added
  5. stirringThe mixture was stirred for 1 hour
  6. customevaporated
  7. dissolutionThe residue was dissolved in THF (3 mL)
  8. stirringThe reaction mixture was stirred for 20 minutes
  9. customevaporated
  10. customThe crude product was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-da8b7c232c3740adb3ba719726210130
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960374B2

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