Methanol → 3-Bromotricyclo[3.3.1.13,7]decane-1-methanol

HRID 588659

Reaction equation

HRID 588659 reaction equation
O1CCCC1.B.CO.[Br:9][C:10]12[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][C:12]([C:20](O)=[O:21])([CH2:13]3)[CH2:11]1)[CH2:17]2>O1CCCC1>[Br:9][C:10]12[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][C:12]([CH2:20][OH:21])([CH2:13]3)[CH2:11]1)[CH2:17]2

Participants

5

Reactant 3

HCID 887MethanolHCID 308183-Bromoadamantane-1-carboxylic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 28029653-Bromotricyclo[3.3.1.13,7]decane-1-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 250 ml round-bottomed flask, 3-bromoadamantane-1-carboxylic acid (7.89 g) was dissolved in tetrahydrofuran (30 mL). Borane tetrahydrofuran complex (1M in hexane, 60 mL) was added slowly. The mixture was stirred at room temperature overnight. Methanol (20 mL) was added to the solution slowly. After removal of the solvents, methanol (5 mL) was added to the oily residue. Removal of the solvent provided the title compound.

Workup

  1. customAfter removal of the solvents, methanol (5 mL)
  2. additionwas added to the oily residue
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-e6c059fa17084a0aa24924dd56f1effb
Source dataset
uspto-grants-2016_01
Patent number
US09227963B2

Linked notes

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