Methanol → HCID 57424234, compound

HRID 1869894Notes

Reaction equation

[CH:1]1([N:4]([CH3:25])[CH:5]2[CH2:14][CH2:13][C:12]([CH3:16])([CH3:15])[C:11]3[CH:10]=[C:9](OS(C(F)(F)F)(=O)=O)[CH:8]=[CH:7][C:6]2=3)[CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:55][OH:56].C(N(CC)CC)C.CN(C)[CH:66]=[O:67]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:55][O:56][C:66]([C:9]1[CH:8]=[CH:7][C:6]2[CH:5]([N:4]([CH:1]3[CH2:3][CH2:2]3)[CH3:25])[CH2:14][CH2:13][C:12]([CH3:16])([CH3:15])[C:11]=2[CH:10]=1)=[O:67]

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of trifluoro-methanesulfonic acid 5-(cyclopropyl-methyl-amino)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl ester (Intermediate 54, 0.37 g, 0.98 mmol), palladium acetate (0.05 g, 0.22 mmol) and 1,3-bis(diphenylphosphino)propane (0.096 g, 0.23 mmol) in a mixture of dimethylformamide (4 mL), methanol (4 mL) and triethyl amine (2 mL) was heated at 70° C. under an atmosphere of carbon monoxide overnight. The volatiles were distilled of in vacuo and the residue was diluted with water and extracted with diethyl ether (×3). The combined organic extract was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to an oil which was subjected to flash column chromatography over silica gel (230-400 mesh) using 2-5% ethyl acetate in hexane as the eluent, to afford the title compound (0.236 g, 85%).

Workup

distillationThe volatiles were distilled of in vacuo
additionthe residue was diluted with water
extractionextracted with diethyl ether (×3)
extractionThe combined organic extract
dry with materialwas dried over anhydrous magnesium sulfate
filtrationfiltered
customevaporated in vacuo to an oil which

Sources & evidence

ORD record: ord-9984cc977ce445cc9a4d9bdeb1ad1b13
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07638648B2

Reaction notes

Loading…