Lithium borohydride → 5-(4-[(4-Phenoxybenzyl)oxy]methylphenyl)isothiazolidin-3-one 1,1-dioxide
Reaction equation
[BH4-].[Li+].[O:3]([C:10]1[CH:32]=[CH:31][C:13]([CH2:14][O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[S:27](=[O:29])(=[O:28])[NH:26][C:25](=[O:30])[CH:24]=3)=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O1CCCC1>[O:3]([C:10]1[CH:32]=[CH:31][C:13]([CH2:14][O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH:23]3[S:27](=[O:29])(=[O:28])[NH:26][C:25](=[O:30])[CH2:24]3)=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1Participants
Procedure
2 M Lithium borohydride in tetrahydrofuran (0.036 mL, 0.072 mmol) was added to 5-(4-[(4-phenoxybenzyl)oxy]methylphenyl)isothiazol-3(2H)-one 1,1-dioxide (40 mg, 0.009 mmol) in tetrahydrofuran (0.5 mL). After stirring for 25 minutes, the reaction was quenched with saturated aqueous ammonium chloride. The product was purified on a 50 mm Luna C18 column using a 20–100% acetonitrile in water gradient with 0.05% trifluoroacetic acid at 30 mL per minute over a 30 minute period. The major product was lyophilized to give a white powder (4 mg, 100%). 1H NMR (400 MHz, CDCl3): δ 7.46 (m, 4H), 7.34 (m, 4H), 7.11 (t, J=7.4 Hz, 1H), 7.01 (m, 4H), 4.98 (t, J=8.4 Hz, 1H), 4.60 (s, 2H), 4.55 (s, 2H), 3.38 (dd, J=8.0 Hz, J′=1.3 Hz, 2H); LCMS found for C23H21NNaO5S (M+Na)+: m/z=446.1.
Workup
- customthe reaction was quenched with saturated aqueous ammonium chloride
- customThe product was purified on a 50 mm Luna C18 column
- customover a 30 minute
Sources & evidence
- ORD record
- ord-7fac1c54c86546f8b5c7a2eef4cf7260
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07141596B2
Reaction notes
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