Sulfuric Acid → HCID 86640527, compound

HRID 2061619Notes

Reaction equation

[CH3:1][C:2]1([CH3:21])[CH2:6][C:5](=[O:7])[N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[N:3]1[CH2:18][C:19]#[CH:20].[BH4-].[Na+].OS(O)(=O)=O>C1COCC1.CCO>[OH:7][CH:5]1[N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[N:3]([CH2:18][C:19]#[CH:20])[C:2]([CH3:21])([CH3:1])[CH2:6]1

Participants

Conditions

Temperature: -20 °C

Procedure

To a stirred solution of 104 (3.0 g, 10.48 mmol) in THF (75 mL) and EtOH (50 mL), sodium borohydride (2.6 g, 68.1 mmol) was added at −20° C. followed by few drops of conc. H2SO4 and stirred for 3 h at −20° C. The reaction mixture was quenched with sat. NaHCO3 solution at −20° C. and allowed to reach room temperature. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in EtOAc. The organic layer was washed with water, dried over Na2SO4 and concentrated under reduced pressure to get crude compound which was purified through silica gel column chromatography, eluted with 15% EtOAc/hexanes to get 105 (2.3 g, 76%). 1H NMR (CDCl3) δ 7.26-7.37 (m, 5H), 5.76 (m, 1H), 5.25 (s, 2H), 3.80-3.60 (m, 3H), 2.48-2.38 (m, 1H), 2.22 (m, 2H), 1.38 (s, 3H), 1.18 (s, 3H).

Workup

customThe reaction mixture was quenched with sat. NaHCO3 solution at −20° C.
customto reach room temperature
concentrationThe reaction mixture was concentrated under reduced pressure
dissolutionthe residue was dissolved in EtOAc
washThe organic layer was washed with water
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customto get crude compound which
customwas purified through silica gel column chromatography
washeluted with 15% EtOAc/hexanes

Sources & evidence

ORD record: ord-feaa1db95373447e998a4cee142fdaba
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08283358B2

Reaction notes

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