(Dimethyl sulfide)trihydroboron → tert-Butyl 2,2-difluoro-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

HRID 1689281Notes

Reaction equation

CSC.B.[F:5][C:6]1([F:25])[C:11](=O)[NH:10][CH2:9][C:8]2([CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)[O:7]1>C1COCC1>[F:25][C:6]1([F:5])[CH2:11][NH:10][CH2:9][C:8]2([CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH2:16][CH2:17]2)[O:7]1

Participants

Conditions

Temperature: 55 °C

Procedure

Borane methyl sulfide complex (2M in THF, 2.69 mL) was added dropwise to a solution of tert-butyl 2,2-difluoro-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate (example 37, step b) (0.55 g) in THF (15 mL). The reaction mixture was heated at 55° C. under nitrogen for 25 minutes and then cooled to room temperature. The mixture was quenched by careful dropwise addition of methanol (5 mL). N1,N2-dimethylethane-1,2-diamine (0.633 g) was then added and the mixture heated at 70° C. for 40 minutes. The solvents were removed under reduced pressure and the residue was purified by flash silica chromatography using 4% methanol in dichloromethane with 1% triethylamine as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 0.32 g. Used directly.

Workup

temperaturecooled to room temperature
customThe mixture was quenched by careful dropwise addition of methanol (5 mL)
additionN1,N2-dimethylethane-1,2-diamine (0.633 g) was then added
temperaturethe mixture heated at 70° C. for 40 minutes
customThe solvents were removed under reduced pressure
customthe residue was purified by flash silica chromatography
customPure fractions were evaporated to dryness

Sources & evidence

ORD record: ord-56c1057ad0114b89a4ff2640b8fd44a5
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148373B2

Reaction notes

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