Sodium Methoxide → (1S,3'R,4'S,5'S,6'R)-5-chloro-6-(4-ethylbenzyl)-6'-(methoxymethyl)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3',4',5'-triol

HRID 1716960Notes

Reaction equation

HRID 1716960 reaction equation
CC1C=CC(S([O:11][CH2:12][C@H:13]2[O:18][C@@:17]3([C:26]4[C:21](=[CH:22][C:23]([Cl:36])=[C:24]([CH2:27][C:28]5[CH:33]=[CH:32][C:31]([CH2:34][CH3:35])=[CH:30][CH:29]=5)[CH:25]=4)[CH2:20][O:19]3)[C@H:16]([OH:37])[C@@H:15]([OH:38])[C@@H:14]2[OH:39])(=O)=O)=CC=1.[CH3:40][O-].[Na+]>>[Cl:36][C:23]1[CH:22]=[C:21]2[C:26](=[CH:25][C:24]=1[CH2:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][CH3:33])=[CH:30][CH:29]=1)[C@:17]1([C@H:16]([OH:37])[C@@H:15]([OH:38])[C@H:14]([OH:39])[C@@H:13]([CH2:12][O:11][CH3:40])[O:18]1)[O:19][CH2:20]2

Participants

3

Reactant 2

HCID 10942334Sodium MethoxideHCID 59013460((1S,3'R,4'S,5'S,6'R)-5-chloro-6-(4-ethylbenzyl)-3',4',5'-trihydroxy-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-6'-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 59013448(1S,3'R,4'S,5'S,6'R)-5-chloro-6-(4-ethylbenzyl)-6'-(methoxymethyl)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3',4',5'-triol

Procedure

To ((1S,3′R,4′S,5′S,6′R)-5-chloro-6-(4-ethylbenzyl)-3′,4′,5′-trihydroxy-3′,4′,5′,6′-tetrahydro-3H-spiro[isobenzofuran-1,2′-pyran]-6′-yl)methyl 4-methylbenzenesulfonate (14 mg, 0.0243 mmol) was added 1 mL of freshly prepared sodium methoxide solution (3 M). After stirring overnight, the reaction was quenched with 2 mL of water. The organic solvent was distilled off and the water layer was extracted with ethyl acetate. The combined organic layers were washed with brine prior to drying over Na2SO4. Concentration under reduced pressure provided the crude product, which was purified by preparative TLC to give 7 mg of title compound. 1H NMR (CD3OD, 400 MHz) δ 7.36 (s, 1H), 7.23 (s, 1H), 7.10 (s, 4H), 5.13 (d, J=13.0 Hz, 1H), 5.07 (d, J=13.0 Hz, 1H), 4.09 (s, 2H), 3.91-3.86 (m, 1H), 3.76-3.67 (m, 2H), 3.62-3.55 (m, 2H), 3.43 (dd, J=10.4, 8.4 Hz, 1H), 3.31 (m, 3H), 2.60 (q, J=7.6 Hz, 2H), 1.20 (t, J=7.6 Hz, 3H); MS ESI (m/z) 435 (M+1)+, calc. 434.

Workup

  1. customthe reaction was quenched with 2 mL of water
  2. distillationThe organic solvent was distilled off
  3. extractionthe water layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialto drying over Na2SO4
  6. concentrationConcentration under reduced pressure
  7. customprovided the crude product, which
  8. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-1d5d5d89c6f145719b1d5d0cf704fc87
Source dataset
uspto-grants-2010_09
Patent number
US07803778B2

Reaction notes

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