Borane;tetrahydrofuran → HCID 67071527, compound

HRID 2262618Notes

Reaction equation

HRID 2262618 reaction equation
[C:1]([N:5]1[CH2:8][CH:7]([C:9]2[N:14]=[CH:13][C:12]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=3)(=[O:18])=[O:17])=[CH:11][CH:10]=2)[CH2:6]1)(=O)[CH2:2][CH3:3].B.C1COCC1>C1COCC1>[CH2:1]([N:5]1[CH2:8][CH:7]([C:9]2[N:14]=[CH:13][C:12]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]([F:28])([F:29])[F:27])=[CH:21][CH:20]=3)(=[O:18])=[O:17])=[CH:11][CH:10]=2)[CH2:6]1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 60205209HCID 60205209, compound

Product 1

HCID 67071527HCID 67071527, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the same procedure as described in Example 46.6, N-[6-(1-propionyl-azetidin-3-yl)-pyridin-3-yl]-4-trifluoromethoxy-benzenesulfonamide (130 mg, 0.30 mmol) in THF (15 ml) was treated with 1M BH3.THF (3 ml). Purification of the crude product by flash column chromatography (CH2Cl2:methanol, 95:5) provides the title compound (75 mg, 60%) as a light yellow oil.

Workup

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

Sources & evidence

ORD record
ord-32128b8b3dd04f9389210f2a52859df8
Source dataset
uspto-grants-2010_12
Patent number
US07851463B2

Reaction notes

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