Diisopropylethylamine → HCID 69893416, compound

HRID 1838299Notes

Reaction equation

HRID 1838299 reaction equation
[C:1]1([CH:7]=[CH:8][C:9]2[CH2:13][CH:12]([CH2:14][CH2:15][CH2:16][CH:17]=O)[O:11][N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH:29]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:12]1[O:11][N:10]=[C:9]([CH:8]=[CH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:13]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 9899402N-(2-Methoxyphenyl)piperazine hydrochlorideHCID 73461814HCID 73461814, compound

Product 1

HCID 69893416HCID 69893416, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[3-(2-Phenylvinyl)-4,5-dihydroisoxazol-5-yl]butanal (23.4 mg, 0.096 mmol), 1-(2-methoxyphenyl)piperazine hydrochloride (20.0 mg, 0.087 mmol), molecular sieve (5 beads), NaBH(OAc)3 (55.6 mg, 0.262 mmol) and diisopropylethylamine (26.9 L, 0.087 mmol) were reacted in 3 mL of methylene chloride for about 12 hr. With the following processes the same as in Example 1, 28.7 mg (73.2%) of the target compound was obtained.

Sources & evidence

ORD record
ord-62401a420bef4c3d83346a692d931973
Source dataset
uspto-grants-2004_01
Patent number
US06673800B2

Reaction notes

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