Methanol → HCID 10130371, compound

HRID 2296629Notes

Reaction equation

HRID 2296629 reaction equation
[O:1]=[C:2]1[N:6]2[CH:7]([CH2:12][CH:13]=[O:14])[CH2:8][CH2:9][CH2:10][CH2:11][C:5]2=[N:4][O:3]1.B.CO>O1CCCC1>[OH:14][CH2:13][CH2:12][CH:7]1[N:6]2[C:2](=[O:1])[O:3][N:4]=[C:5]2[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 887MethanolHCID 6331BoraneHCID 9837040HCID 9837040, compound

Product 1

HCID 10130371HCID 10130371, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Example 8 (3.0 g, 0.015 mol) in tetrahydrofuran (20 mL) was added a borane. THF complex (20 mL, 0.020 mol). The reaction stirred for 2 hours upon which methanol (19 mL) was added. The solvent was removed under reduced pressure. The resulting oil was partioned between CH2Cl2 (40 mL) and water (2×20 mL). The organic layer was dried over magnesium sulfate and all solvent was removed under reduced pressure. The residue was chromatographed eluting with 1:1 ethyl acetate/hexane to produce 2.1 g (69%) of the title material. 1H NMR (CDCl3, 300 MHz) d 1.18-2.15(m, 8H), 3.59(m, 2H), 4.39(m, 1H). 13C NMR (CDCl3, 75 MHz) d 24.45, 25.71, 26.47, 32.56, 34.67, 51.16, 58.85, 160.66, 160.89.

Workup

  1. additionwas added
  2. customThe solvent was removed under reduced pressure
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customall solvent was removed under reduced pressure
  5. customThe residue was chromatographed
  6. washeluting with 1:1 ethyl acetate/hexane

Sources & evidence

ORD record
ord-be7e953ff1a44eab88e38c12cdf6e957
Source dataset
uspto-grants-2002_12
Patent number
US06489323B1

Reaction notes

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