Pyridine → tert-Butyl (7-cyano-1,2,3,4-tetrahydronaphthalen-2-yl)(2-oxoethyl)carbamate

HRID 1466053Notes

Reaction equation

[CH2:1]([N:4]([CH:12]1[CH2:21][CH2:20][C:19]2[C:14](=[CH:15][C:16]([C:22]#[N:23])=[CH:17][CH:18]=2)[CH2:13]1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:2]=C.N1C=CC=CC=1.[O:30]=[O+][O-]>C(Cl)Cl.CO>[C:22]([C:16]1[CH:15]=[C:14]2[C:19]([CH2:20][CH2:21][CH:12]([N:4]([CH2:1][CH:2]=[O:30])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:13]2)=[CH:18][CH:17]=1)#[N:23]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of tert-butyl allyl(7-cyano-1,2,3,4-tetrahydronaphthalen-2-yl)carbamate (320 mg, 1.0 mmol) in 1:1 CH2Cl2/MeOH (20 mL) containing pyridine (0.16 mL, 2.0 mmol) was cooled to −78° C., and O3 was passed through until a blue color was present. N2 was then bubbled through to discharge the blue color and Me2S (3 ml) was added. The reaction mixture was allowed to warm and left overnight. The mixture was washed with 1 N HCl and aqueous NaHCO3 and then dried and concentrated to give the title compound. MS m/z: 315 [M+1]+.

Workup

customN2 was then bubbled through
additionwas added
temperatureto warm
washThe mixture was washed with 1 N HCl and aqueous NaHCO3
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-e2c0c1163f7d4d7c9047462af8ca1f05
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999990B2

Reaction notes

Loading…