Diisopropylethylamine → HCID 18753382, compound

HRID 1838282Notes

Reaction equation

HRID 1838282 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH2:10][CH:9]([CH2:11][CH2:12][CH:13]=O)[O:8][N:7]=1.Cl.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]1[CH2:29][CH2:28][N:27]([CH2:13][CH2:12][CH2:11][CH:9]2[O:8][N:7]=[C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)[CH2:10]2)[CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 9899402N-(2-Methoxyphenyl)piperazine hydrochlorideHCID 18753391HCID 18753391, compound

Product 1

HCID 18753382HCID 18753382, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(3-(2-Thienyl)-4,5-dihydroisoxazol-5-yl)propanal (21.6 mg, 0.096 mmol), 1-(2-methoxyphenyl)piperazine hydrochloride (20.0 mg, 0.087 mmol), molecular sieve (5 beads), NaBH(OAc)3 (55.5 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, 31.0 mg (92.3%) of the target compound was obtained.

Sources & evidence

ORD record
ord-81b10d864b164757aa9d79eac6a80522
Source dataset
uspto-grants-2004_01
Patent number
US06673800B2

Reaction notes

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