Sodium triacetoxyborohydride → HCID 58933801, compound

HRID 854291Notes

Reaction equation

HRID 854291 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9]([C:11]2[CH:12]=[N:13][NH:14][CH:15]=2)=[O:10])[CH2:3][CH2:2]1.[C:16]1([C@@H:22]2[CH2:24][C@H:23]2[CH:25]=O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[C:16]1([C@@H:22]2[CH2:24][C@H:23]2[CH2:25][N:1]2[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9]([C:11]3[CH:15]=[N:14][NH:13][CH:12]=3)=[O:10])[CH2:3][CH2:2]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 12323031Cyclopropanecarboxaldehyde, 2-phenyl-, (1R,2R)- (9CI)HCID 58933866HCID 58933866, compound

Product 1

HCID 58933801HCID 58933801, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1H-pyrazole-4-carboxylic acid (piperidin-4-ylmethyl)-amide (290 mg, 1.39 mmol), trans-2-phenylcyclopropanecarbaldehyde (224 mg, 1.53 mmol) and sodium triacetoxyborohydride (590 mg, 2.78 mmol) in MeOH (15 mL) was heated to 50° C. and stirred for 1 h. The resulting reaction mixture was concentrated and purified by silica gel chromatography (gradient: CH2Cl2 to 80:20:2 CH2Cl2:MeOH:NH4OH) to give the trans 1H-pyrazole-4-carboxylic acid [1-(2-phenyl-cyclopropylmethyl)-piperidin-4-ylmethyl]-amide product.

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated
  3. custompurified by silica gel chromatography (gradient: CH2Cl2 to 80:20:2 CH2Cl2:MeOH:NH4OH)

Sources & evidence

ORD record
ord-81e28890fafb49d1bebcd98d7dceafdb
Source dataset
uspto-grants-2007_08
Patent number
US07259157B2

Reaction notes

Loading…