Water → 1,3-dihydro-1-hydroxy-N,3,3-trimethyl-2,1-Benzoxaborole-6-methanamine

HRID 1037011Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1037011
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([CH:11]=O)[CH:9]=[CH:10][C:5]=2[C:4]([CH3:14])([CH3:13])[O:3]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH3:29][NH2:30].O>C1COCC1.C(O)(=O)C>[CH3:13][C:4]1([CH3:14])[O:3][B:2]([OH:1])[C:6]2[CH:7]=[C:8]([CH2:11][NH:30][CH3:29])[CH:9]=[CH:10][C:5]1=2

Komponenten

7

Edukt 4

HCID 962WaterHCID 6329MethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 866854601-Hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbaldehyde

Produkt 1

HCID 866854591,3-dihydro-1-hydroxy-N,3,3-trimethyl-2,1-Benzoxaborole-6-methanamineAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbaldehyde (370 mg, 1.95 mmol) in THF (15 mL) at rt was added NaBH(OAc)3 (827 mg, 3.9 mmol) followed by methylamine alcoholic solution (30%, 1.0 mL). Several drops of acetic acid were added to the reaction mixture to pH of 6. The mixture was continued to stir at rt overnight. Water (20 mL) was added and the mixture was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by prep-HPLC to give 3,3-dimethyl-6-((methylamino)methyl)benzo[c][1,2]oxaborol-1(3H)-ol (300 mg; yield 75%) as a colorless oil. MS: m/z=206.1 (M+1, ESI+).

Aufarbeitung

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by prep-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-cbcbe7bc4b184a709de773f67ba2d986
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546357B2

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