Methanol → HCID 11523755, compound

HRID 254239Notes

Reaction equation

HRID 254239 reaction equation
[CH3:1][O:2][P:3]([CH2:6][CH2:7][CH2:8][C:9]1([CH3:28])[CH2:18][CH2:17][C:16]2[C:11](=[C:12]3[CH:26]4[CH2:27][CH:23]([CH2:24][CH2:25]4)[C:13]3=[C:14]([O:19]COC)[CH:15]=2)[O:10]1)(=[O:5])[OH:4].[CH3:29]O>Cl>[CH3:29][O:4][P:3]([CH2:6][CH2:7][CH2:8][C:9]1([CH3:28])[CH2:18][CH2:17][C:16]2[C:11](=[C:12]3[CH:26]4[CH2:27][CH:23]([CH2:24][CH2:25]4)[C:13]3=[C:14]([OH:19])[CH:15]=2)[O:10]1)(=[O:5])[O:2][CH3:1]

Participants

4

Reactant 2

HCID 887MethanolHCID 86597203HCID 86597203, compound

Product 1

HCID 11523755HCID 11523755, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

190 mg of 6-methoxymethoxy-dimethyl phosphonate derivative from Step 3 was treated with a mixture of 20 mL of MeOH and 20 drops of concentrate HCl for overnight. After removal of most of the solvent, ethyl acetate was added and then washed with water, and dried over MgSO4. After the removal of solvents the residue was purified by flash column chromatography on silica gel (10% MeOH I DCM) to afford 90 mg of [3-(6-hydroxy-2-methyl-3,4,7,8,9,10-hexahydro-7,10-methano-2H-benzo[h]chromen-2-yl)-propyl]-phosphonic acid dimethyl ester. 1H-NMR (300 MHz, CDCl3) δ (ppm): 6.38 (s, 1H), 5.32 (s, 1H), 3.72-3.82 (m, 6H) 3.50-3.54 (m, 2H), 2.62-2.68 (m, 4H), 1.70-1.84 (m, 12H), 1.22-1.28 (s, 3H) MS: 381 (M+H+, 100%), 403 (M+Na+, 36%)

Workup

  1. customAfter removal of most of the solvent, ethyl acetate
  2. additionwas added
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. customAfter the removal of solvents the residue
  6. customwas purified by flash column chromatography on silica gel (10% MeOH I DCM)

Sources & evidence

ORD record
ord-8826bce664d24d919fbb8537b56057ce
Source dataset
uspto-grants-2011_01
Patent number
US07875607B2

Reaction notes

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