Borane → 4-(4-Fluorophenyl)-3-piperidinemethanol

HRID 2084606Notes

Reaction equation

HRID 2084606 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=O)[NH:11][CH2:10][CH:9]2[CH2:15]CC(O)=O)=[CH:4][CH:3]=1.B.[O:21]1CCCC1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH:9]2[CH2:15][OH:21])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6331BoraneHCID 8028Tetrahydrofuran2×HCID 227338414-(4-Fluorophenyl)-3-carboxyethylpiperidin-6-one

Product 1

HCID 98156874-(4-Fluorophenyl)-3-piperidinemethanolYield 80%

Procedure

Borane-tetrahydrofuran complex (1.0 molar solution in tetrahydrofuran (10.8 ml, 10.8 mmol) was added over 20 hours in 3 stages (in 3.6 mmol portions) at a rate of 7 ml/hour by means of a syringe pump to a solution of 4-(4-fluorophenyl)-3-carboxyethylpiperidin-6-one (0.53 g, 2 mmol, trans/cis˜1:1) in tetrahydrofuran (3 ml) at 26° C. The reaction mixture was stirred for 1 hour after addition of the last portion of the borane solution. then quenched with 3.5 ml 30% aqueous potassium carbonate solution. The phases were separated and the aqueous phase extracted with diethyl ether (25 ml). The organic phases were combined and evaporated to yield 0.43 g of the title compound. Yield 80%.

Workup

  1. customthen quenched with 3.5 ml 30% aqueous potassium carbonate solution
  2. customThe phases were separated
  3. extractionthe aqueous phase extracted with diethyl ether (25 ml)
  4. customevaporated

Sources & evidence

ORD record
ord-2de98012b2964442a08b87848972df21
Source dataset
uspto-grants-2004_04
Patent number
US06716985B2

Reaction notes

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