Borane;tetrahydrofuran → 1-(4-Methoxybenzyl)-2-oxo-1,2-dihydro-3-chloro-4-methoxycarbonyl-5-hydroxymethyl-pyridine

HRID 1752594Notes

Reaction equation

HRID 1752594 reaction equation
B.C1COCC1.[CH3:7][O:8][C:9]1[CH:30]=[CH:29][C:12]([CH2:13][N:14]2[CH:19]=[C:18]([C:20](O)=[O:21])[C:17]([C:23]([O:25][CH3:26])=[O:24])=[C:16]([Cl:27])[C:15]2=[O:28])=[CH:11][CH:10]=1>CO>[CH3:7][O:8][C:9]1[CH:30]=[CH:29][C:12]([CH2:13][N:14]2[CH:19]=[C:18]([CH2:20][OH:21])[C:17]([C:23]([O:25][CH3:26])=[O:24])=[C:16]([Cl:27])[C:15]2=[O:28])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 904220291-(4-Methoxybenzyl)-2-oxo-1,2-dihydro-3-chloro-4-methoxycarbonyl-pyridine-5-carboxylic acid

Product 1

HCID 904219461-(4-Methoxybenzyl)-2-oxo-1,2-dihydro-3-chloro-4-methoxycarbonyl-5-hydroxymethyl-pyridineYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A BH3-THF solution (100 ml, 100 mmol) was added carefully to compound (10) (8.4 g, 23.88 mmol) in a 100 ml round-bottomed flask. The resulting solution was stirred at about r. t. overnight. MeOH was added. The solution was concentrated to dryness to give the title compound (8.15 g, 23.89 mmol, 100% yield) as a yellow solid. LC-MS (ESI+): m/e 338(M+H)+, Rt: 1.65 min.

Workup

  1. customovernight
  2. concentrationThe solution was concentrated to dryness

Sources & evidence

ORD record
ord-d51d33ce6b3740dbb829ec2b2f06b383
Source dataset
uspto-grants-2015_10
Patent number
US09163019B2

Reaction notes

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