(Diethylamino)sulfur trifluoride → HCID 58661631, compound

HRID 1487010Notes

Reaction equation

[CH:1]([N:14]1[CH2:17][C:16](O)([C:18]#[N:19])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(S(F)(F)[F:27])CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH:1]([N:14]1[CH2:17][C:16]([F:27])([C:18]#[N:19])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

1-Benzhydryl-3-hydroxyazetidine-3-carbonitrile (10.5 g, 39.7 mmol) was dissolved in DCM and cooled to −78° C. DAST (12.80 g, 79.45 mmol) was slowly added and the reaction mixture was allowed to warm to rt where it was further stirred for 5 h. Reaction mixture was cooled to 0° C. and transferred into 500 mL NaHCO3 solution and extracted with (100 mL×3) DCM. Combined organic layers were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to obtain 15.0 g of crude product, which was purified by chromatography to obtain 6.0 g of 1-benzhydryl-3-fluoroazetidine-3-carbonitrile. (57.14% yield). 1H NMR (400 MHz, CDCl3, ppm) δ=7.6-7.1 (m, 10H); 4.46 (s, 1H); 3.9-3.6 (m, 2H); 3.5-3.2 (m, 2H).

Workup

temperatureto warm to rt where it
customReaction mixture
temperaturewas cooled to 0° C.
extractionextracted with (100 mL×3) DCM
washCombined organic layers were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customto obtain 15.0 g of crude product, which
customwas purified by chromatography

Sources & evidence

ORD record: ord-7bd0de4c76af4d2f93b7f77cfa928d2e
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428490B2

Reaction notes

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