2,6,6-Trimethylbicyclo[3.1.1]heptane-1,2-diol → HCID 86747608, compound

HRID 1975637Notes

Reaction equation

HRID 1975637 reaction equation
[C:1]12([OH:12])[CH2:9][CH:5]([C:6]1([CH3:8])[CH3:7])[CH2:4][CH2:3][C:2]2([OH:11])[CH3:10].[CH3:13][O:14][CH2:15][CH2:16][CH2:17][B:18]([O-:20])[O-:19]>C1COCC1>[C:1]12([OH:12])[CH2:9][CH:5]([C:6]1([CH3:8])[CH3:7])[CH2:4][CH2:3][C:2]2([OH:11])[CH3:10].[CH3:13][O:14][CH2:15][CH2:16][CH2:17][B:18]([O-:20])[O-:19]

Participants

4

Reactant 2

HCID 219250472,6,6-Trimethylbicyclo[3.1.1]heptane-1,2-diolHCID 86747609HCID 86747609, compound

Product 1

HCID 86747608HCID 86747608, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Methoxy-1-propene (6.0 g, 83.3 mMol) is reacted with catecholborane (10.0 g, 83.3 mMol) at 100° C. over 24 hr. The crude product is distilled in vacuo to give 3-methoxy-propane-1-boronate as a colourless oil. (+)-Pinanediol(10.6 g, 62.5 g mMol) is dissolved in THF and the above synthesized 3-methoxy-propane-1-boronate (12.0 g, 62.5 mMol) is added. After 1 hr at room temperature, the THF is removed in vacuo and the residue is purified by flash chromatography (80:20 hexane/EtOAc) to give (+)-pinanediol-3-methoxy-propane-1-boronate as a colourless oil.

Workup

  1. additionis added
  2. customthe THF is removed in vacuo
  3. customthe residue is purified by flash chromatography (80:20 hexane/EtOAc)

Sources & evidence

ORD record
ord-5fcb07b49f8a4296a6bd1e5044f83e1c
Source dataset
uspto-grants-1994_02
Patent number
US05288707

Reaction notes

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