Diethyl Ether → HCID 86586650, compound

HRID 2088117Notes

Reaction equation

[CH2:1]([N:8]1[C@@H:13]2[C@H:14]([C:16]3[N:20]([CH3:21])[N:19]=[N:18][N:17]=3)[CH2:15][C@@:9]1([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C@H:10]([O:22][C:23](=O)[C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=1)[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:45](OCC)C>C1(C)C=CC=CC=1.C[Ti](C)(C1C=CC=C1)C1C=CC=C1>[CH2:1]([N:8]1[C@@H:13]2[C@H:14]([C:16]3[N:20]([CH3:21])[N:19]=[N:18][N:17]=3)[CH2:15][C@@:9]1([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C@H:10]([O:22][C:23]([C:24]1[CH:25]=[C:26]([C:34]([F:36])([F:37])[F:35])[CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)=[CH2:45])[CH2:11][CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Dimethylbis(cyclopentadienyl)titanium (12 ml, 0.45M solution in toluene) was added to a solution of (1R*,2R*,5S*,6R*)-8-benzyl-2-[3,5-bis(trifluoromethyl)benzoyloxy]-6-(1-methyl-1H-tetrazol-5-yl)-1-phenyl-8-azabicyclo[3.2.1]octane (Description 33b; 0.83 g, 1.35 mmol) in toluene (20 ml). The mixture was stirred at 100° C. for 3 hours. On cooling to room temperature the mixture was poured into 100 ml of 1:1 diethyl ether:iso-hexanes. The mixture was filtered through Celite™and the filtrate concentrated in vacuo. The residue was chromatographed on silica gel eluting with 10, 20 and 50% ethyl acetate/iso-hexanes to yield the title compound (0.57 g, 69%).

Workup

temperatureOn cooling to room temperature the mixture
filtrationThe mixture was filtered through Celite™and the filtrate
concentrationconcentrated in vacuo
customThe residue was chromatographed on silica gel eluting with 10, 20 and 50% ethyl acetate/iso-hexanes

Sources & evidence

ORD record: ord-1dae23b2a2414f9b95b393f271927d63
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06727249B2

Reaction notes

Loading…