Borane;tetrahydrofuran → 2(1H)-Quinolinone, 5-[(1R)-2-chloro-1-hydroxyethyl]-8-(phenylmethoxy)-
Reaction equation
B.O1CCCC1.CB1N2CCC[C@@H]2C(C2C=CC=CC=2)(C2C=CC=CC=2)O1.[CH2:28]([O:35][C:36]1[CH:37]=[CH:38][C:39]([C:47](=[O:50])[CH2:48][Cl:49])=[C:40]2[C:45]=1[NH:44][C:43](=[O:46])[CH:42]=[CH:41]2)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O1CCCC1>[CH2:28]([O:35][C:36]1[CH:37]=[CH:38][C:39]([C@@H:47]([OH:50])[CH2:48][Cl:49])=[C:40]2[C:45]=1[NH:44][C:43](=[O:46])[CH:42]=[CH:41]2)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
Borane-tetrahydrofuran complex (1M in tetrahydrofuran, 1 ml, 1 mMol) was added dropwise to a solution of (R)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo [1,2-c][1,3,2]oxazaborole (0.1 equiv, 30 mg, 0.1 mMol) in tetrahydrofuran (6 ml) at ambient temperature under an argon atmosphere. After 5 minutes, 8-benzyloxy-5-chloroacetylcarbostyril (328 mg, 1 mMol) was added and the reaction mixture was stirred for a further 15 minutes. The reaction mixture was cooled to 5° C. and quenched by the dropwise addition of methanol (2 ml). The quenched reaction mixture was stirred for 15 minutes at 5° C. and for 30 minutes at ambient temperature. The solvent was evaporated and the residue was purified by chromatography on silica gel eluting with 10% methanol in ethyl acetate to afford the title compound as a pale yellow solid; m.p. 148°-149° C.; [α]D25 -9.0° (c=1, methanol).
Workup
- customquenched by the dropwise addition of methanol (2 ml)
- customThe quenched reaction mixture
- stirringwas stirred for 15 minutes at 5° C. and for 30 minutes at ambient temperature
- customThe solvent was evaporated
- customthe residue was purified by chromatography on silica gel eluting with 10% methanol in ethyl acetate
Sources & evidence
- ORD record
- ord-16b39d2cbe2a47a1b4de2d047b306c67
- Source dataset
- uspto-grants-1998_05
- Patent number
- US05750701
Reaction notes
Loading…