Borane;tetrahydrofuran → HCID 10108872, compound

HRID 1827146Notes

Reaction equation

HRID 1827146 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][NH:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21]([C:25](O)=[O:26])[CH:20]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.O1CCCC1>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([CH2:17][NH:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21]([CH2:25][OH:26])[CH:20]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 23577249HCID 23577249, compound

Product 1

HCID 10108872HCID 10108872, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of 4-[(1-benzyloxycarbonyl-piperidin-4-ylmethyl)-amino]-pyridine-2-carboxylic acid (0.59 gm, 0.0016 mol) in THF (2 mL) under nitrogen was added a solution of 1.0M borane-tetrahydrofuran (6 mL) and the mixture allowed to stir at room temperature for 1 h. The reaction was cooled to 0° C., quenched with 1N HCl (10 mL), concentrated and diluted with 10% aqueous sodium bicarbonate. Extraction with dichloromethane (2×50 mL)and concentration of the organic layer gave 540 mg of crude material. Column chromatography using dichloromethane/methanol/ammonium hydroxide—90/10/2 and crystallization from diethyl ether gave 4-[(2-hydroxymethyl-pyridin-4-ylamino)-methyl]-piperidine-1-carboxylic acid benzyl ester.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. customquenched with 1N HCl (10 mL)
  3. concentrationconcentrated
  4. additiondiluted with 10% aqueous sodium bicarbonate
  5. extractionExtraction with dichloromethane (2×50 mL)and concentration of the organic layer
  6. customgave 540 mg of crude material
  7. customdichloromethane/methanol/ammonium hydroxide—90/10/2 and crystallization from diethyl ether

Sources & evidence

ORD record
ord-66730ebaf9804485a36e02d755ce28da
Source dataset
uspto-grants-2006_05
Patent number
US07053089B2

Reaction notes

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