Lithium borohydride → HCID 22145918, compound

HRID 1994316Notes

Reaction equation

HRID 1994316 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](OCC)=[O:9])[CH:5]=[C:4]([Cl:13])[C:3]=1[NH:14][C:15](=[O:30])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:17]=1.[BH4-].[Li+]>O1CCCC1.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([Cl:13])[C:3]=1[NH:14][C:15](=[O:30])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29]2)[CH:17]=1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 22145785HCID 22145785, compound

Product 1

HCID 22145918HCID 22145918, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A stirred solution of N-(2,6-dichloro-4-ethoxycarbonylphenyl)-3-cyclopentyloxy-4-methoxybenzamide (6.1 g) in dry tetrahydrofuran (80 mL) at room temperature under argon is treated dropwise with a solution of lithium borohydride in tetrahydrofuran (115 mL; 2 M). The mixture is stirred overnight and then it is treated portionwise with saturated brine (200 mL) and stirred for 30 minutes. The organic layer is then washed with water, dried over magnesium sulfate and evaporated. The resulting residue is subjected to flash chromatography on silica gel, to give N-(2,6-dichloro-4-hydroxymethylphenyl)-3-cyclopentyloxy-4-methoxybenzamide (4.4 g), m.p. 174-176° C. [Elemental analysis: C, 57.1; H, 5.4; N, 2.9%. calculated C20H21O4NCl2:0.5H2O: C, 57.3; H, 5.3; N, 3.3%].

Workup

  1. stirringstirred for 30 minutes
  2. washThe organic layer is then washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-4022b28cd99848059453d42f185e467a
Source dataset
uspto-grants-2010_01
Patent number
US07652144B2

Reaction notes

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