Diisopropylethylamine → HCID 22727360, compound

HRID 2086434Notes

Reaction equation

HRID 2086434 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:15]=[C:14]([CH2:16][CH2:17][CH:18]=O)[O:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl.Cl[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]1[CH2:33][CH2:32]C[CH2:30][CH2:29]1.C([N:37](C(C)C)CC)(C)C.[BH-](OC(C)=O)(OC(C)=O)[O:44][C:45]([CH3:47])=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:15]=[C:14]([CH2:16][CH2:17][CH2:18][N:37]3[CH2:30][CH2:29][N:28]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[O:44][CH2:45][CH3:47])[CH2:33][CH2:32]3)[O:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 22727343HCID 22727343, compoundHCID 23153645HCID 23153645, compound

Product 1

HCID 22727360HCID 22727360, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

About 2 min after dissolving 3-[3-(3,4-dimethoxyphenyl)isoxazol-5-yl]propanal (22.1 mg, 0.09 mmol), (2-chlorophenyl)piperidine HCl (20.6 mg, 0.09 mmol), and diisopropylethyl amine (14.8, 0.09 mmol) in 2 mL of dry methylene chloride, were added NaBH(OAc)3 (54.0 mg, 0.26 mmol) and molecular sieves (5 beads). The reaction mixture was reacted for 20 hr and followed the same processes as in Example 1 to obtain 28.5 mg (74.2%) of the target compound.

Workup

  1. customThe reaction mixture was reacted for 20 hr

Sources & evidence

ORD record
ord-c3ac2a1ffabe457aa17683db64728827
Source dataset
uspto-grants-2004_04
Patent number
US06723724B2

Reaction notes

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