Sodium borohydride → 2-(1-Piperidinylmethyl)-1-azabicyclo[2.2.2]octan-3-ol

HRID 327392Notes

Reaction equation

HRID 327392 reaction equation
[N:1]1([CH2:7][CH:8]2[C:13](=[O:14])[CH:12]3[CH2:15][CH2:16][N:9]2[CH2:10][CH2:11]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+]>C(O)C>[N:1]1([CH2:7][CH:8]2[CH:13]([OH:14])[CH:12]3[CH2:11][CH2:10][N:9]2[CH2:16][CH2:15]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 191084152-(1-Piperidinylmethyl)-1-azabicyclo[2.2.2]octan-3-one

Product 1

HCID 191083992-(1-Piperidinylmethyl)-1-azabicyclo[2.2.2]octan-3-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 2-(1-piperidinylmethyl)-1-azabicyclo-[2.2.2]octan-3-one (8.90 g, 40 mmoles) in absolute ethanol (40 ml) was treated dropwise with a solution of sodium borohydride (1.15 g, 30.4 mmoles) in absolute ethanol (40 ml). The solution was stirred at room temperature for 18 hours, concentrated in vacuo, and diluted with water (100 ml). The aqueous solution was treated with potassium carbonate and extracted with ether, and the combined organic extracts were dried (MgSO4) and concentrated in vacuo. The residual solid was recrystallized from acetonitrile to afford 3.32 g (37%) of the trans isomer as colorless crystals, mp 130°-131° C.

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with water (100 ml)
  3. additionThe aqueous solution was treated with potassium carbonate
  4. extractionextracted with ether
  5. dry with materialthe combined organic extracts were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residual solid was recrystallized from acetonitrile
  8. customto afford 3.32 g (37%) of the trans isomer as colorless crystals, mp 130°-131° C.

Sources & evidence

ORD record
ord-7125ac8d6b49492da0487bf64d49929b
Source dataset
uspto-grants-1993_12
Patent number
US05273972

Reaction notes

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