Borane;tetrahydrofuran → HCID 178419202, compound

HRID 1608577Notes

Reaction equation

HRID 1608577 reaction equation
[CH3:1][N:2]([CH3:14])[C:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][C:5]([OH:13])([CH2:6]3)[CH2:4]1)[CH2:10]2.[BH3:15].C1COCC1>C1COCC1>[CH3:1][N:2]([CH3:14])[C:3]12[CH2:10][CH:9]3[CH2:8][CH:7]([CH2:6][C:5]([OH:13])([CH2:11]3)[CH2:4]1)[CH2:12]2.[BH3:15]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 2941673HCID 2941673, compound

Product 1

HCID 178419202HCID 178419202, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To N,N-dimethyl-3-hydroxytricyclo-[3.3.1.13,7 ]decan-1-amine (1.3 g; 0.0067 mole) dissolved in THF, under N2 and chilled in ice, is added borane-THF (14 ml; 0.014 mole) over 5 min. The ice bath is removed after an additional 5 min. and stirred at room temperature for 3 hrs. To this mixture is added ether (100 ml), washed with saturated NaHCO3 and evaporated to dryness to give borane N,N-dimethyl-3-hydroxytricyclo[3.3.1.13,7 ]decan-1-amine complex which is used directly in Step C.

Workup

  1. temperaturechilled in ice
  2. customThe ice bath is removed after an additional 5 min.
  3. additionTo this mixture is added ether (100 ml)
  4. washwashed with saturated NaHCO3
  5. customevaporated to dryness
  6. customto give borane N,N-dimethyl-3-hydroxytricyclo[3.3.1.13,7 ]decan-1-amine complex which

Sources & evidence

ORD record
ord-c0476fe75f4b4da794c730935c31a09c
Source dataset
uspto-grants-1995_03
Patent number
US05395846

Reaction notes

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