Diglyme → HCID 11676256, compound

HRID 636268Notes

Reaction equation

HRID 636268 reaction equation
[C:1]([C@@H:5]1[CH2:10][C@H:9]([O:11][Si:12]([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]([CH3:29])=[CH:7][CH2:6]1)([O:3][CH3:4])=[O:2].C[O:31]CCOCCOC>>[Si:12]([O:11][C@@H:9]1[C@H:8]([CH3:29])[C@@H:7]([OH:31])[CH2:6][C@H:5]([C:1]([O:3][CH3:4])=[O:2])[CH2:10]1)([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 8150DiglymeHCID 11589598HCID 11589598, compound

Product 1

HCID 11676256HCID 11676256, compound

Conditions

Temperature
0 °C

Procedure

To a stirred solution of this cyclohexene (110 mg, 0.27 mmol) in 2 ml of diglyme at 0° C. was added dropwise a borane-THF complex solution (1.0 M, 325 μL, 0.325 mmol, 1.5 eq). The resulting solution was stirred for 4 h at 0° C. THF was removed and TAO (trimethyl amine N-oxide, 90 mg, 0.81 mmol) was added. The mixture was heated and refluxed for 2 h. The resulting mixture was cooled to room temperature, extracted with EtOAc (4×40 ml) and dried over MgSO4. The residue was separated by flash chromatography on silica, then was purified by HPLC (Cyclohexane/EtOAc: 9:1) to afford compound 3.2.c (R=Me, P=TBDPS, A=COOCH3) (46 g, 40.5%) as a colorless oil.

Workup

  1. customTHF was removed
  2. additionTAO (trimethyl amine N-oxide, 90 mg, 0.81 mmol) was added
  3. temperatureThe mixture was heated
  4. temperaturerefluxed for 2 h
  5. temperatureThe resulting mixture was cooled to room temperature
  6. extractionextracted with EtOAc (4×40 ml)
  7. dry with materialdried over MgSO4
  8. customThe residue was separated by flash chromatography on silica
  9. customwas purified by HPLC (Cyclohexane/EtOAc: 9:1)

Sources & evidence

ORD record
ord-8821b0b3723b4029a6ecb73bbf065f7a
Source dataset
uspto-grants-2001_02
Patent number
US06191292B1

Reaction notes

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