ChemicalBook CAS DataBase List METHYL 4-HYDROXYMETHYLCUBANECARBOXYLATE

METHYL 4-HYDROXYMETHYLCUBANECARBOXYLATE synthesis

7synthesis methods

Product Name:METHYL 4-HYDROXYMETHYLCUBANECARBOXYLATE
CAS Number:60462-19-3
Molecular formula:C11H12O3
Molecular Weight:192.21

24539-28-4
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$140.00/25mg

60462-19-3
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$319.00/100mg

Yield: 100%

Reaction Conditions:

Stage #1:4-(methoxycarbonyl)-1-cubanecarboxylic acid with borane in tetrahydrofuran at -78 - -70; for 4 h;
Stage #2: with water at 20; for 0.5 h;

Steps:

2.2 Example 2: Preparation 2: 4-methoxycarbonyl-l- (hydroxymethyl) cubane
The mono acid (8) (0.48 g) is dissolved in dry THF (5 mL) and cooled [TO-70 °C.] A solution [OF BH3] in THF is added slowly with stirring. The reaction mixture is stirred at-78 °C for 4 hrs and allowed to come to room temperature. Water (3 mL) is added and stirred for 30 min, potassium carbonate (0.85 g) is added and the solution extracted with [ET20.] The organic phase is dried over magnesium sulfate and evaporated to give the alcohol (9) 0.46 g (100%). m. p. [83-85 °C.'H] NMR (200 MHz, solvent) [5] : 1.58 (s, 1H), 3.62 (s, 3H), 3.72 (s, 2H), 3.81 (m, 3H), 4.1 (m, 3H).

References:

PRESCIENT NEUROPHARMA INC. WO2004/24709, 2004, A2 Location in patent:Page 49-50