Diisopropylethylamine → HCID 22727346, compound

HRID 2086443Notes

Reaction equation

HRID 2086443 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:15]=[C:14]([CH:16](C)[CH2:17][CH:18]=O)[O:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl.[CH3:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N:29]1[CH2:34][CH2:33]C[CH2:31][CH2:30]1.[CH:35]([N:38](C(C)C)CC)(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:10][O:9][C:8]1[CH:7]=[CH:6][C:5]([C:11]2[CH:15]=[C:14]([CH2:16][CH2:17][CH2:18][CH2:35][N:38]3[CH2:33][CH2:34][N:29]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[CH3:22])[CH2:30][CH2:31]3)[O:13][N:12]=2)=[CH:4][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 22727348HCID 22727348, compoundHCID 69890936HCID 69890936, compound

Product 1

HCID 22727346HCID 22727346, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

About 2 min after dissolving 3-[3-(3,4-dimethoxyphenyl)isoxazol-5-yl]butanal (34.4 mg, 0.125 mmol), 1-(2-methylphenyl)piperidine HCl (24.2 mg, 0.114 mmol) and diisopropylethyl amine (19.9, 0.114 mmol) in 2 mL of dry methylene chloride, were added NaBH(OAc)3 (72.5 mg, 0.342 mmol) and molecular sieves (5 beads). The reaction mixture was reacted for 3 hr and followed the same processes as in Example 1 to obtain 30.5 mg (61.4%) of the target compound.

Workup

  1. customThe reaction mixture was reacted for 3 hr

Sources & evidence

ORD record
ord-8764da41ee0f4b69b63a8a7b0077f36c
Source dataset
uspto-grants-2004_04
Patent number
US06723724B2

Reaction notes

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