Ethyl Acetate → HCID 67071277, compound

HRID 2262623Notes

Reaction equation

HRID 2262623 reaction equation
[C:1]([N:5]1[CH2:8][CH:7]([C:9]2[CH: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.C(OCC)(=O)C>C1COCC1>[CH2:1]([N:5]1[CH2:8][CH:7]([C:9]2[CH: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)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2723981Borane;tetrahydrofuranHCID 60205210HCID 60205210, compound

Product 1

HCID 67071277HCID 67071277, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the same procedure as described in Example 47.2, N-[4-(1-propionyl-azetidin-3-yl)-phenyl]-4-trifluoromethoxy-benzenesulfonamide (170 mg, 0.39 mmol) in THF (20 ml) was then treated with 1M BH3.THF (3.9 ml). The crude material was chromatographied (ethyl acetate) to afford the title compound (86 mg, 52%) as a pale yellow oil.

Sources & evidence

ORD record
ord-a9326d7e0dd242728ab96c730f84f97e
Source dataset
uspto-grants-2010_12
Patent number
US07851463B2

Reaction notes

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