Binap, (A+-)- → HCID 131734735, compound

HRID 1775333Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.CC(C)([O-])C.[Na+].[NH2:15][CH:16]1[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:15][CH:16]2[CH2:17][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19]2)[CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 2-bromo-4-methylpyridine (90 mg, 0.523 mmol), sodium tert-butoxide (101 mg, 1.046 mmol), tert-butyl 3-aminoazetidine-1-carboxylate (451 mg, 2.62 mmol) and BINAP (16.3 mg, 0.026 mmol) in anhydrous toluene (7 ml) was purged with argon. Palladium(II)acetate (5.9 mg, 0.026 mmol) was added and the mixture was stirred at 100° C. overnight in a closed vial. After cooling to room temperature the mixture was filtered through kieselguhr and concentrated under reduced pressure. The residue was purified by column chromatography (silica, gradient from 0.5 to 10% ethyl acetate in heptane) to afford 60 mg of a solid (0.228 mmol, 43%) MS (ESI) m/z=264.2 [M+1]+.

Workup

temperatureAfter cooling to room temperature the mixture
filtrationwas filtered through kieselguhr
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography (silica, gradient from 0.5 to 10% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-32d4f258b1c94d08875193dec05c3b07
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260441B2

Reaction notes

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