Borane;tetrahydrofuran → HCID 68915560, compound

HRID 870358Notes

Reaction equation

HRID 870358 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:15]=[N:16][C:17]3[CH2:18][CH2:19][CH2:20][CH:21]([NH:24][C:25](=O)[CH2:26][CH3:27])[C:22]=3[CH:23]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].B.C1COCC1>C1COCC1>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:15]=[N:16][C:17]3[CH2:18][CH2:19][CH2:20][CH:21]([NH:24][CH2:25][CH2:26][CH3:27])[C:22]=3[CH:23]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 68915298HCID 68915298, compound

Product 1

HCID 68915560HCID 68915560, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the same procedure as described above, N-[3-(4-isopropylbenzenesulfonylamino)-5,6,7,8-tetrahydro-quinolin-5-yl]-propionamide (136 mg, 0.33 mmol) in THF (10 ml) was treated with 1M BH3.THF (3.3 ml). Purification of the crude product by flash column chromatography (heptane:ethyl acetate, 1:2) provides the title compound (74 mg, 56%) as a white solid.

Workup

  1. customPurification of the crude product by flash column chromatography (heptane:ethyl acetate, 1:2)

Sources & evidence

ORD record
ord-6c1c69da3ef142a7b26a138922f54bc8
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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