Methanol → HCID 66673635, compound

HRID 870274Notes

Reaction equation

HRID 870274 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-3da62ad931984f3b97dfdff5aabb06a1
Source dataset
uspto-grants-2015_03
Patent number
US08969370B2

Reaction notes

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