Diethyl aminosulfur trifluoride → HCID 178454071, compound

HRID 271340Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8](O)[CH2:9][O:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:13][CH2:12]1.C(S(F)(F)([F:32])(CC)N)C>ClCCl>[F:32][CH:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])[CH2:9][O:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:13][CH2:12]1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 18 g of tert-butyl {trans-4-[2-(2-fluorophenyl)-2-hydroxyethoxy]-cyclohexyl}carbamate in 200 mL of dichloromethane was added over 30 min to a solution of 23 g of diethyl-amino sulfur-trifluoride in 800 mL of dichloromethane cooled to −78° C. under nitrogen atmosphere. The mixture was allowed stir for 1 h at −78° C. then quenched with 100 mL of saturated sodium carbonate. After stirring for 15 min the layers were separated. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. Chromatography over silica gel eluting with a gradient of 2%-25% ethyl acetate in hexane gave 12 g of product as a white crystalline solid: 1H NMR (400 MHz, CDCl3) 7.45 (m, 1H), 7.3 (m, 1H), 7.2 (m, 1H), 7.06 (m, 1H), 5.15 (dm, JH-F=48 Hz), 4.18 (br s, 1H), 3.65 (complex m, 2H), 3.42 (br s, 1H), 3.3 (m, 1H), 2.0 (d, 4H), 1.42 (s, 9H), 1.4 (q, 2H), 1.15 (q, 2H).

Workup

customthen quenched with 100 mL of saturated sodium carbonate
stirringAfter stirring for 15 min the layers
customwere separated
dry with materialThe organic layer was dried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-0a54aa168b9a44b48d0e65eddf5983ec
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07452893B2

Reaction notes

Loading…