Ethyl orthoformate → HCID 86759433, compound

HRID 2088199Notes

Reaction equation

[NH2:1][C@@H:2]1[CH2:8][C@:7]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:9]([CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C@H:3]1[CH2:4][CH2:5][C@H:6]2[O:23][C@H:24]([C:26]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([C:36]([F:39])([F:38])[F:37])[CH:27]=1)[CH3:25].[CH2:40](OC(OCC)OCC)C.[N-:50]=[N+:51]=[N-:52].[Na+]>C(O)(=O)C>[CH2:10]([N:9]1[C@@H:3]2[C@H:2]([N:1]3[CH:40]=[N:52][N:51]=[N:50]3)[CH2:8][C@@:7]1([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C@H:6]([O:23][C@H:24]([C:26]1[CH:27]=[C:28]([C:36]([F:39])([F:37])[F:38])[CH:29]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:31]=1)[CH3:25])[CH2:5][CH2:4]2)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 90 °C

Procedure

(1R*,2R*,5S*,6R*)-6-Amino-8-benzyl-2-{(1S*)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-1-phenyl-8-azabicyclo[3.2.1]octane (Example 132; 150 mg, 0.27 mmol) in glacial acetic acid (2 ml) with triethylorthoformate (3 ml) was heated to 90° C. Sodium azide (178 mg, 2.74 mmol) was then added and the mixture stirred at 90° C. overnight. The reaction mixture was cooled and partitioned between saturated sodium hydrogen carbonate solution and dichloromethane and the organics dried (MgSO4) and concentrated in vacuo to give the title compound as a yellow oil (158 mg, 95%).

Workup

temperatureThe reaction mixture was cooled
custompartitioned between saturated sodium hydrogen carbonate solution and dichloromethane
dry with materialthe organics dried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d975f2de8c524efdb3bf6406f3138424
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06727249B2

Reaction notes

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