Diisopropylethylamine → HCID 22727333, compound

HRID 2086430Notes

Reaction equation

HRID 2086430 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:21][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)OC(C)=O.[Na+]>C(Cl)Cl>[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]1[CH2:33][CH2:32][N:37]([CH2:18][CH2:17][CH2:16][C:14]2[O:13][N:12]=[C:11]([C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:15]=2)[CH2:30][CH2:29]1

Participants

6

Reactant 4

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

Product 1

HCID 22727333HCID 22727333, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

About 2 min after dissolving 3-[3-(3,4-dimethoxyphenyl)isoxazol-5-yl]propanal (34.0 mg, 0.13 mmol), (2-chlorophenyl)piperidine HCl (25.2 mg, 0.11 mmol), and diisopropylethyl amine (18.8, 0.11 mmol) in 2 mL of dry methylene chloride, were added NaBH(OAc)3 (68.7 mg, 0.32 mmol) and molecular sieves (5 beads). The reaction mixture was reacted for 22 hr and followed the same processes as in Example 1 to obtain 39.8 mg (82.0%) of the target compound.

Workup

  1. customThe reaction mixture was reacted for 22 hr

Sources & evidence

ORD record
ord-e9a631c0b83140728d4e387c5a7a9c7e
Source dataset
uspto-grants-2004_04
Patent number
US06723724B2

Reaction notes

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