Methanol → HCID 66673635, compound

HRID 1880805Notes

Reaction equation

HRID 1880805 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C@@H:4]([CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[CH2:5][C:6](O)=[O:7].B.CO>O1CCCC1>[CH3:1][O:2][C:3](=[O:16])[C@@H:4]([CH2:9][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)[CH2:5][CH2:6][OH:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 6331BoraneHCID 22831490(S)-2-(Cyclohexylmethyl)succinic acid-1-methyl ester

Product 1

HCID 66673635HCID 66673635, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of (S)-2-cyclohexylmethyl-succinic acid 1-methyl ester (484 mg, 2.12 mmol) and tetrahydrofuran 10 mL) was stirred at room temperature and then cooled to 0° C. To the reaction mixture was added 1.0 M borane in tetrahydrofuran (4.2 mL) dropwise over 5 min. After 2 h, MeOH was added drop-wise to quench the reaction. The reaction mixture was stirred for 30 min at room temperature and then concentrated to dryness. The crude residue was suspended in MeOH, concentrated to dryness, and purified on SiO2 (40 g) using 5-10% MeOH/DCM as eluent to provide the title compound (0.32 g) as a clear oil: 1H NMR (CDCl3, 400 mHz) δ (ppm): 3.69-3.65 (m, 5H), 2.65 (m, 1H), 1.85-1.59 (m, 8H), 1.32-1.12 (m, 5H), 0.87 (m, 2H).

Workup

  1. temperaturecooled to 0° C
  2. customto quench
  3. customthe reaction
  4. stirringThe reaction mixture was stirred for 30 min at room temperature
  5. concentrationconcentrated to dryness
  6. concentrationconcentrated to dryness
  7. custompurified on SiO2 (40 g)

Sources & evidence

ORD record
ord-f7000387ae1d446d83d5042a55854faf
Source dataset
uspto-grants-2012_11
Patent number
US08318765B2

Reaction notes

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