Sodium Hydroxide → Methyl 3-hydroxymethyltricyclo[3.3.1.1 3,7]decane-1-carboxylate

HRID 1820304Notes

Reaction equation

HRID 1820304 reaction equation
[C:1]12([C:15](OC)=[O:16])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][C:3]([C:11]([O:13][CH3:14])=[O:12])([CH2:4]3)[CH2:2]1)[CH2:8]2.[H-].C([Al+]CC(C)C)C(C)C.[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.O>[OH:16][CH2:15][C:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][C:3]([C:11]([O:13][CH3:14])=[O:12])([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 365223Dimethyl 1,3-adamantanedicarboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 18410517Methyl 3-hydroxymethyltricyclo[3.3.1.1 3,7]decane-1-carboxylateYield 19%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

After dissolving dimethyl 1,3-adamantanedicarboxylate (1.00 g, 3.96 mmol) in tetrahydrofuran (5 mL), diisobutylaluminum hydride (0.95 M; 5.0 mL, 4.75 mmol) was added dropwise while cooling on ice, and then the mixture was further stirred for 3 hours while cooling on ice. After the reaction, water (0.2 mL) and then aqueous 15% NaOH (0.2 mL) were added dropwise at room temperature, and the mixture was stirred for 30 minutes. Next, water (0.6 mL) and anhydrous magnesium sulfate were added and stirred therewith, and the insoluble portion was filtered out. The solvent was distilled off under reduced pressure, and the obtained residue was subjected to chromatography (50 g Merck Art. 9385, hexane:ethyl acetate=3:2) to obtain the title compound as a colorless oil (0.1648 g, 0.735 mmole) (19% yield).

Workup

  1. additionwas added dropwise
  2. temperaturewhile cooling on ice
  3. temperaturewhile cooling on ice
  4. stirringthe mixture was stirred for 30 minutes
  5. stirringstirred
  6. filtrationthe insoluble portion was filtered out
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-c918402f014e4d6fa8474455522d93bb
Source dataset
uspto-grants-2009_10
Patent number
US07601843B2

Reaction notes

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