Diisopropylethylamine → HCID 10157069, compound

HRID 2086431Notes

Reaction equation

HRID 2086431 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:10]=[C:9]([CH2:11][CH2:12][CH:13]=O)[O:8][N:7]=1.Cl.[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]1[CH2:28][CH2:27]C[CH2:25][CH2:24]1.C([N:32](C(C)C)CC)(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]1[CH2:28][CH2:27][N:32]([CH2:13][CH2:12][CH2:11][C:9]2[O:8][N:7]=[C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)[CH:10]=2)[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 22727325HCID 22727325, compoundHCID 23153645HCID 23153645, compound

Product 1

HCID 10157069HCID 10157069, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

About 2 min after dissolving 3-(3-(2-thienyl)isoxazol-5-yl)propanal (27.8 mg, 0. 13 mmol), (2-chlorophenyl)piperidine HCl (26.0 mg, 0.11 mmol), and diisopropylethyl amine (19.5, 0.11 mmol) in 2 mL of dry methylene chloride, were added NaBH(OAc)3 (71.2 mg, 0.34 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 41.4 mg (95.4%) of the target compound.

Workup

  1. customThe reaction mixture was reacted for 22 hr

Sources & evidence

ORD record
ord-bb126fa591b64d738a45f5692921c42e
Source dataset
uspto-grants-2004_04
Patent number
US06723724B2

Reaction notes

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