Diisopropylethylamine → HCID 10273366, compound

HRID 2086429Notes

Reaction equation

HRID 2086429 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([CH2:13][CH2:14][CH:15]=O)[O:10][N:9]=2)=[CH:4][CH:3]=1.Cl.[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:25]1[CH2:30][CH2:29]C[CH2:27][CH2:26]1.C([N:34](C(C)C)CC)(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][N:34]3[CH2:29][CH2:30][N:25]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[Cl:18])[CH2:26][CH2:27]3)[O:10][N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 22727338HCID 22727338, compoundHCID 23153645HCID 23153645, compound

Product 1

HCID 10273366HCID 10273366, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

About 2 min after dissolving 3-[3-(4-chlorophenyl)isoxazol-5-yl]propanal (27.3 mg, 0.12 mmol), (2-chlorophenyl)piperidine HCl (22.6 mg, 0.10 mmol), and diisopropylethyl amine (16.9, 0.10 mmol) in 2 mL of dry methylene chloride, were added NaBH(OAc)3 (61.7 mg, 0.29 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 36.4 mg (90.3%) of the target compound.

Workup

  1. customThe reaction mixture was reacted for 22 hr

Sources & evidence

ORD record
ord-67b3f8fd51e04aa7be57fd5a62c2a432
Source dataset
uspto-grants-2004_04
Patent number
US06723724B2

Reaction notes

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