Hydrochloric Acid → Methyl 4-(3-hydroxypropyl)bicyclo[2.2.2]octane-1-carboxylate

HRID 1784509Notes

Reaction equation

HRID 1784509 reaction equation
[CH3:1][O:2][C:3]([C:5]12[CH2:12][CH2:11][C:8]([CH2:13][CH2:14][C:15](O)=[O:16])([CH2:9][CH2:10]1)[CH2:7][CH2:6]2)=[O:4].B.Cl>O1CCCC1>[OH:16][CH2:15][CH2:14][CH2:13][C:8]12[CH2:9][CH2:10][C:5]([C:3]([O:2][CH3:1])=[O:4])([CH2:12][CH2:11]1)[CH2:6][CH2:7]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 225917033-[4-(Methoxycarbonyl)bicyclo[2.2.2]oct-1-yl]propanoic acid

Product 1

HCID 22591716Methyl 4-(3-hydroxypropyl)bicyclo[2.2.2]octane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Carboxylic acid 11-3 (400 mg, 1.67 mmol) was dissolved in tetrahydrofuran (5 mL) and borane (1 M solution in THF, 2.17 mL, 1.3 eq.) was added dropwise at room temperature. After 2 h the reaction was added to 50 mL of 1 N HCl and then extracted three times with 50 mL of methylene chloride. The combined organic layers were dried over magnesium sulfate and the solvent was removed under reduced pressure to afford crude methyl 4-(3-hydroxypropyl)bicyclo[2.2.2]octane-1-carboxylate (11-4) which was used without purification in the next step. 1H NMR (500 MHz, CD3OD): δ 3.66 (3H, s), 3.62 (2H, t, J=6.5 Hz), 1.78 (6H, m), 1.50 (2H, m), 1.41 (2H, m), 1.17 (2H, m) ppm.

Workup

  1. extractionextracted three times with 50 mL of methylene chloride
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9617c9127714410590c90029d8cad091
Source dataset
uspto-grants-2009_03
Patent number
US07504402B2

Reaction notes

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