Lithium tri-s-butylborohydride → 2-[[(1R,2S,4R,5R)-5-hydroxy-2-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-propan-2-yl-1,3-thiazol-4-one
Reaction equation
[CH:1]([C:4]1([CH3:19])[S:8][C:7]([NH:9][C@H:10]2[CH2:15][C@H:14]3[CH2:16][C@@H:11]2[CH2:12][C:13]3=[O:17])=[N:6][C:5]1=[O:18])([CH3:3])[CH3:2].CCC(C)[BH-](C(C)CC)C(C)CC.[Li+]>C1COCC1>[OH:17][C@@H:13]1[CH2:12][C@H:11]2[CH2:16][C@@H:14]1[CH2:15][C@@H:10]2[NH:9][C:7]1[S:8][C:4]([CH:1]([CH3:3])[CH3:2])([CH3:19])[C:5](=[O:18])[N:6]=1Participants
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 5-isopropyl-5-methyl-2-((1R,2S,4R)-5-oxobicyclo[2.2.1]heptan-2-ylamino)thiazol-4(5H)-one (0.380 g, 1.36 mmol) in anhydrous THF (20 mL) was added L-Selectride (1.0 M solution in THF, 4.07 mL, 4.07 mmol) in anhydrous THF at −78° C. under nitrogen. After stirring at −78° C. for 3 h., the reaction was quenched with hydrogen peroxide (35 wt % solution in water, 4 mL) and NaOH (10% aqueous, 7 mL). The mixture was warmed to ambient temp. and then in a 65° C. bath overnight. The volatiles were removed in vacuo. The residue was partitioned between CHCl3/i-PrOH (v/v=3/1) and brine. The organic portion was separated, dried over MgSO4, filtered, and conc. in vacuo. The residue was purified by flash column chromatography (0 to 5% of MeOH in EtOAc) to give the title compound as a white solid.
Workup
- customthe reaction was quenched with hydrogen peroxide (35 wt % solution in water, 4 mL) and NaOH (10% aqueous, 7 mL)
- temperatureThe mixture was warmed to ambient temp.
- customin a 65° C.
- customovernight
- customThe volatiles were removed in vacuo
- customThe residue was partitioned between CHCl3/i-PrOH (v/v=3/1) and brine
- customThe organic portion was separated
- dry with materialdried over MgSO4
- filtrationfiltered
- customThe residue was purified by flash column chromatography (0 to 5% of MeOH in EtOAc)
Sources & evidence
- ORD record
- ord-e6a8ea5a29674a0db764728a4b7c435a
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08541592B2
Reaction notes
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