Sulfuric acid magnesium salt (1:1) → HCID 57307820, compound

HRID 1737058Notes

Reaction equation

HRID 1737058 reaction equation
[CH2:1]([C@@H:8]1[CH2:13][C@@H:12]([NH2:14])[CH2:11][CH2:10][N:9]1[C:15](=[O:24])[C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[CH:27]=[C:26]1[CH:34]=O.S([O-])([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>C1(C)C=CC=CC=1.CO>[CH2:1]([C@@H:8]1[CH2:13][C@@H:12]([NH:14][CH2:34][C:26]2[O:25][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[CH:27]=2)[CH2:11][CH2:10][N:9]1[C:15](=[O:24])[C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 613412-BenzofurancarboxaldehydeHCID 4311764Sodium borohydrideHCID 53839030(2R*,4S*)-2-benzyl-1-(3,5-dichlorobenzoyl)-4-piperidinamine

Product 1

HCID 57307820HCID 57307820, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

200 mg (0.551 mmol) of (2R*,4S*)-2-benzyl-1-(3,5-dichlorobenzoyl)-4-piperidinamine are reacted in analogy to Example 2g with 97 mg (0.661 mmol) of benzofuran-2-carboxaldehyde and 90 mg of magnesium sulfate in 2 ml of toluene and subsequently reduced with 22 mg (0.584 mmol) of sodium borohydride in 2 ml of methanol. The title compound ##STR93## is obtained (150 mg, 55%) as oil. TLC: methylene chloride/methanol/conc. ammonia (2000:50:1) Rf =0.18, FD-MS: M+ =492, 494. IR: 1630 cm-1.

Sources & evidence

ORD record
ord-b8560e94695c418da5e78519525e4822
Source dataset
uspto-grants-1996_07
Patent number
US05541195

Reaction notes

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