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

HRID 1791048노트

반응식

HRID 1791048 반응식
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

참가 물질

7

반응물 5

HCID 24346Disodium disulfiteHCID 72879MethanesulfonamideHCID 22042256HCID 22042256, 화합물HCID 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)2회

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-2bc99a6f11a2488abd035af078d29166
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071340B2

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