Sodium Hydroxide → HCID 59858086, compound

HRID 2378376Notes

Reaction equation

HRID 2378376 reaction equation
C[O:2][C:3](=[O:23])[CH2:4][CH2:5][C:6]1([CH3:22])[CH2:15][CH2:14][C:13]2[C:8](=[C:9]3[CH:20]4[CH2:21][CH:17]([CH2:18][CH2:19]4)[C:10]3=[C:11]([OH:16])[CH:12]=2)[O:7]1.[OH-].[Na+].O1CCO[CH2:28][CH2:27]1>O>[OH:16][C:11]1[CH:12]=[C:13]2[C:8](=[C:9]3[CH:20]4[CH2:27][CH2:28][CH2:21][CH:17]([CH2:18][CH2:19]4)[C:10]=13)[O:7][C:6]([CH2:5][CH2:4][C:3]([OH:2])=[O:23])([CH3:22])[CH2:15][CH2:14]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 11716671HCID 11716671, compound

Product 1

HCID 59858086HCID 59858086, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3-(6-Hydroxy-2-methyl-3,4,7,8,9,10-hexahydro-7,10-methano-2H-benzo[h]chromen-2-yl)-propionic acid methyl ester (235 mg, 0.68 mmol) in 5 mL of dioxane was added a solution of NaOH (41 mg, 1.02 mmol) in 400 mL water. The resulting suspension was vigorously stirred for 15 h and quenched by adding 50 mL of saturated NaH2PO4 solution. The mixture was extracted with EtOAc (3×50 mL) and the organic layers were dried over Na2SO4 and concentrated. The crude product was purified by chromatography on silica gel to afford 3-(6-hydroxy-2-methyl-3,4,7,8,9,10-hexahydro-7,10-propano-2H-benzo[h]chromen-2-yl)-propionic acid as a white sticky solid (184 mg). 1H-NMR (CDCl3, 300 MHz) δ (ppm): 7.71 (ws, 1 H), 6.41 (s, 1 H), 3.54 (m, 1 H), 3.38 (m, 1 H), 2.73 )m, 2 H), 2.56 (m, 2 H), 2.10-1.62 (m, 12 H), 0.95 (m, 5 H); 13C-NMR δ (ppm): 180.1, 144.0, 142.9, 132.8 128.9, 118.5, 112.7, 74.0, 34.48, 34.0, 32.0, 31.9, 31.8, 29.5, 28.7, 28.6, 26.4, 26.3, 26.0, 23.9, 23.3, 22.7, 22.3; MS (ESI) m/z: 331 (M+H+, 100%).

Workup

  1. customquenched
  2. additionby adding 50 mL of saturated NaH2PO4 solution
  3. extractionThe mixture was extracted with EtOAc (3×50 mL)
  4. dry with materialthe organic layers were dried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-b264e4c5aae24b8cb32ab68c74b7161b
Source dataset
uspto-grants-2008_12
Patent number
US07470798B2

Reaction notes

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