Disodium disulfite → Methyl 3-hydroxy-3-(hydroxymethyl)-2,3-dihydro-1-benzoxepin-7-carboxylate

HRID 1791048Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1791048
CC[C@H]1[C@H]2C[C@H]([C@H](OC3C4C(=CC=CC=4)C(O[C@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:22]C)C=C4)N(CC2)C1.CS(N)(=O)=O.C=C1C=[CH:70][C:69]2[CH:72]=[C:73]([C:76]([O:78][CH3:79])=[O:77])[CH:74]=[CH:75][C:68]=2[O:67]C1.S(OS([O-])=O)([O-])=O.[Na+].[Na+].[C:89]([OH:93])([CH3:92])([CH3:91])[CH3:90].O>ClCCl>[OH:93][C:89]1([CH2:92][OH:22])[CH:91]=[CH:70][C:69]2[CH:72]=[C:73]([C:76]([O:78][CH3:79])=[O:77])[CH:74]=[CH:75][C:68]=2[O:67][CH2:90]1

Komponenten

7

Edukt 5

HCID 24346Disodium disulfiteHCID 72879MethanesulfonamideHCID 22042256HCID 22042256, VerbindungHCID 510036741-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazineHCID 714019492-Methylpropan-2-ol--water (1/1)2×

Produkt 1

HCID 22042276Methyl 3-hydroxy-3-(hydroxymethyl)-2,3-dihydro-1-benzoxepin-7-carboxylateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

21 g (7 equivalents) of AD-mix-α and 1.31 g (13.8 mmol) of methanesulfonamide dissolved in 75 ml of a 1/1 tert-butyl alcohol/water mixture are added at ambient temperature to 3 g (13.8 mmol) of methyl 3-methylene-2,3-dihydro-1-benzoxepin-7-carboxylate, prepared according to example 35, in suspension in 20 ml of a 1/1 tert-butyl alcohol/water mixture. The reaction medium is stirred for 4 days and is then treated with 2.6 g of sodium disulfite. The medium is reextracted with dichloromethane and the organic phases are washed with brine. After evaporating, the crude reaction product is purified by chromatography on silica gel (ethyl acetate/heptane 50/50) to give 3.2 g (100%) of methyl 3-hydroxy-3-(hydroxymethyl)-2,3-dihydro-1-benzoxepin-7-carboxylate in the form of a colorless honey; 1H NMR (300 MHz, CDCl3): 7.88 (d, J=2.4 Hz, 1H), 7.81 (dd, J=2.4 Hz and 8.4 Hz, 1H), 6.98 (d, J=8.4 Hz, 1H), 6.37 (d, J=12 Hz, 1H), 5.88 (d, J=12 Hz, 1H), 4.24 (dd, J=1.2 Hz and 11.7 Hz, 1H), 4.01 (d, J=11.7 Hz, 1H), 3.87 (s, 3H), 3.69 and 3.60 (2d, J=11.4 Hz, 2H).

Aufarbeitung

  1. customprepared
  2. washthe organic phases are washed with brine
  3. customAfter evaporating
  4. customthe crude reaction product
  5. customis purified by chromatography on silica gel (ethyl acetate/heptane 50/50)

Quellen und Nachweise

ORD-Eintrag
ord-2bc99a6f11a2488abd035af078d29166
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07071340B2

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