Borane → HCID 86759700, compound

HRID 2179968Notes

Reaction equation

B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@H]2N1CCC2.B.[CH3:23][C:24]([O:27][C:28](=[O:39])[NH:29][CH2:30][CH2:31][C:32]([C:34]1[CH:38]=[CH:37][O:36][CH:35]=1)=[O:33])([CH3:26])[CH3:25]>O1CCCC1>[CH3:26][C:24]([O:27][C:28](=[O:39])[NH:29][CH2:30][CH2:31][C@H:32]([C:34]1[CH:38]=[CH:37][O:36][CH:35]=1)[OH:33])([CH3:23])[CH3:25]

Participants

Conditions

Temperature: 0 °C

Procedure

(S)-2-Methyl-CBS-oxazaborolidine (1M in toluene, 0.84 ml, 0.836 mmol) was added to anhydrous tetrahydrofuran (50 ml) and the solution cooled to 0° C. Borane:tetrahydrofuran complex (1M, 5.02 ml, 5.02 mmol) was then added dropwise, keeping the temperature at 0° C. The mixture was stirred for 15 minutes then added the product of step (a) (2.0 g, 8.36 mmol) as a solution in tetrahydrofuran (50 ml), dropwise over 1 h keeping the temperature at 0° C. Stirred overnight whilst allowing to warm to room temperature. The reaction was quenched with methanol (5 ml) and stirred for a half hour. The solvent was removed in vacuo and another aliquot of methanol (20 ml) added. The solvent was removed in vacuo and the residue chromatographed on flash silica, eluting with hexane:ethyl acetate (1:1), to give the title compound as a colourless oil (1.685 g, 84%).

Workup

customat 0° C
waitdropwise over 1 h keeping
customat 0° C
stirringStirred overnight
temperatureto warm to room temperature
customThe reaction was quenched with methanol (5 ml)
stirringstirred for a half hour
customThe solvent was removed in vacuo
additionanother aliquot of methanol (20 ml) added
customThe solvent was removed in vacuo
customthe residue chromatographed on flash silica
washeluting with hexane:ethyl acetate (1:1)

Sources & evidence

ORD record: ord-778f967ee5ee43b9b9c1b26ebd09e25c
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06887871B2

Reaction notes

Loading…