HCID 21839617, compound → HCID 86747605, compound

HRID 1975635Notes

Reaction equation

HRID 1975635 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].[Br:13][CH2:14][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].[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][B:18]([O-:20])[O-:19]

Participants

4

Reactant 2

HCID 21839617HCID 21839617, compoundHCID 219250472,6,6-Trimethylbicyclo[3.1.1]heptane-1,2-diol

Product 1

HCID 86747605HCID 86747605, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Bromo-1-butene (20.8 ml, 203.3 mMol) is reacted with catecholborane (24,4 g, 203,3 mMol) at 100° C. over 16 hr. The crude product is distilled in vacuo to give 4-bromo-butane-1-boronate as a white crystalline compound. (+)-Pinanediol (27.7 g, 163 mMol) is dissolved in THF and the above synthesized 4-bromo-butane-1-boronate (41.6 g, 163 mMol) is added. After 1 hr at room temperature, the THF is removed in vacuo and the residue is purified by flash chromatrography (90:10 hexane/EtOAc) to give (+)-pinanediol-4-bromo-butane-1-boronate as a colourless oil.

Workup

  1. additionis added
  2. customthe THF is removed in vacuo
  3. customthe residue is purified by flash chromatrography (90:10 hexane/EtOAc)

Sources & evidence

ORD record
ord-81034adbd3b4493a9178ddcf2a552b67
Source dataset
uspto-grants-1994_02
Patent number
US05288707

Reaction notes

Loading…