Chloroform → HCID 88040420, compound

HRID 2088213Notes

Reaction equation

O[O:2][S:3]([O-:5])=O.[K+].[CH2:7]([N:14]1[C@@H:19]2[C@H:20]([C:22]3[N:23]=[N:24][N:25]([CH2:27]SC)[N:26]=3)[CH2:21][C@@:15]1([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C@H:16]([O:30][CH2:31][C:32]1[CH:37]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:35]=[C:34]([C:42]([F:45])([F:44])[F:43])[CH:33]=1)[CH2:17][CH2:18]2)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH:52](Cl)(Cl)Cl>>[CH2:7]([N:14]1[C@@H:19]2[C@H:20]([C:22]3[N:23]=[N:24][N:25]([CH2:27][S:3]([CH3:52])(=[O:5])=[O:2])[N:26]=3)[CH2:21][C@@:15]1([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C@H:16]([O:30][CH2:31][C:32]1[CH:37]=[C:36]([C:38]([F:39])([F:40])[F:41])[CH:35]=[C:34]([C:42]([F:44])([F:45])[F:43])[CH:33]=1)[CH2:17][CH2:18]2)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Reactant 3

HCID 6212Chloroform

HCID 23707502Potassium hydroxy sulfite

HCID 88040330HCID 88040330, compound

Product 1

HCID 88040420HCID 88040420, compoundYield 68%

Conditions

Temperature: 50 °C

Procedure

Oxone® (370 mg, 0.6 mmol) was added to a suspension of (1R*,2R*,5S*,6R*)-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(2-methylthiomethyl-2H-tetrazol-5-yl)-1-phenyl-8-azabicyclo[3.2.1]octane (Compound 3 g in Table 3; 130 mg, 0.2 mmol) and wet alumina (200 mg) in chloroform (10 ml). The mixture was heated to 50° C. for 18 hours, then filtered through Celite™ and the filtrate concentrated in vacuo to yield the title compound (92 mg, 68%).

Workup

filtrationfiltered through Celite™
concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record: ord-96fb7aea061b4284900385b4ea2276ee
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06727249B2

Reaction notes

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