Borane;tetrahydrofuran → HCID 11494783, compound

HRID 870357Notes

Reaction equation

HRID 870357 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][CH:19]([NH:24][C:25](=O)[CH2:26][CH3:27])[CH2:20][CH2:21][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][CH:19]([NH:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][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 68914711HCID 68914711, compound

Product 1

HCID 11494783HCID 11494783, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the same procedure as described above, N-[3-(4-isopropylbenzenesulfonylamino)-5,6,7,8-tetrahydro-quinolin-7-yl]-propionamide (90 mg, 0.22 mmol) in THF (5 ml) was treated with 1M BH3.THF (2.2 ml). Purification of the crude product by flash column chromatography (CH2Cl2:MeOH, 95:5) provides the title compound (52 mg, 60%) as a white solid.

Workup

  1. customPurification of the crude product by flash column chromatography (CH2Cl2:MeOH, 95:5)

Sources & evidence

ORD record
ord-8eaab2e5334946e5b22283c5c5b0006a
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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