Ethyl Acetate → 4-Isopropyl-N-[4-(1-propyl-azetidin-3-yl)-phenyl]-benzene sulfonamide

HRID 1260237Notes

Reaction equation

HRID 1260237 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH:20]3[CH2:23][N:22]([C:24](=O)[CH2:25][CH3:26])[CH2:21]3)=[CH:16][CH:15]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(OCC)(=O)C>C1COCC1>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH:20]3[CH2:21][N:22]([CH2:24][CH2:25][CH3:26])[CH2:23]3)=[CH:16][CH:15]=2)(=[O:11])=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 536286634-Isopropyl-N-[4-(1-propionyl-azetidin-3-yl)-phenyl]-benzenesulfonamide

Product 1

HCID 536286624-Isopropyl-N-[4-(1-propyl-azetidin-3-yl)-phenyl]-benzene sulfonamideYield 67.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Following the same procedure as described in Example 46.6, 4-isopropyl-N-[4-(1-propionyl-azetidin-3-yl)-phenyl]-benzenesulfonamide (140 mg, 0.36 mmol) in THF (18 ml) was then treated with 1M BH3. THF (3.6 ml). The crude material was chromatographied (ethyl acetate) to afford the title compound (90 mg, 67%) as a pale yellow oil.

Sources & evidence

ORD record
ord-b1e898f444434df78325b3c5456a607c
Source dataset
uspto-grants-2013_06
Patent number
US08470810B2

Reaction notes

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