Borane;tetrahydrofuran → HCID 86702092, compound

HRID 715834Notes

Reaction equation

HRID 715834 reaction equation
[Br:1][C:2]12[CH2:12][C:6]3([C:13](O)=[O:14])[CH2:7][C:8]([CH3:11])([CH2:10][C:4]([CH3:16])([CH2:5]3)[CH2:3]1)[CH2:9]2.O1CCCC1.B>O1CCCC1>[Br:1][C:2]12[CH2:12][C:6]3([CH2:13][OH:14])[CH2:5][C:4]([CH3:16])([CH2:10][C:8]([CH3:11])([CH2:7]3)[CH2:9]1)[CH2:3]2

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 3738693HCID 3738693, compound

Product 1

HCID 86702092HCID 86702092, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-3,7-dimethyltricyclo[3.3.1.13,7]decane-1-carboxylic acid (4.57 g, 15.9 mmol) in tetrahydrofuran (10 mL) was added borane tetrahydrofuran complex (50 mL, 1 M in THF) dropwise and the mixture was stirred at room temperature for 14 hours. The reaction mixture was quenched with methanol, concentrated and purified by normal phase chromatography to provide the title compound.

Workup

  1. customThe reaction mixture was quenched with methanol
  2. concentrationconcentrated
  3. custompurified by normal phase chromatography

Sources & evidence

ORD record
ord-820518a7276c426fac0fd34fd51d4edc
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

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