6-Oxabicyclo[3.1.0]hexane → HCID 68454320, compound

HRID 2356212Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)(=[O:10])=[O:9].[CH:17]12[O:22][CH:21]1[CH2:20][CH2:19][CH2:18]2>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:16][CH2:15][N:14]([C@@H:20]2[CH2:19][CH2:18][CH2:17][C@H:21]2[OH:22])[CH2:13][CH2:12]1)(=[O:9])=[O:10]

Participants

Conditions

Temperature: 80 °C

Procedure

1-(2-Chlorophenylsulfonyl)piperizine (1 eq, 0.19 mmol) was dissolved in ethyl alcohol (2 ml), then treated with 6-oxa-bicyclo[3,1,0]hexane (2eq, 0.38 mmol), the reaction solution was heated to 80° C. for 8 hour. The reaction mixture was purified by prep-HPLC. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.36-1.48 (m, 1 H), 1.49-1.74 (m, 3 H), 1.81-2.03 (m, 2 H), 2.52-2.67 (m, 3 H), 2.68-2.78 (m, 2 H), 3.28-3.37 (m, 4 H), 3.99-4.18 (m, 1 H), 7.33-7.42 (m, 1 H), 7.44-7.58 (m, 2 H), 7.98 (d, J=8.21, 1.14 Hz, 1 H); ESI-MS: m/z 345 (m+H)+.

Workup

customThe reaction mixture was purified by prep-HPLC

Sources & evidence

ORD record: ord-aa86387b82f049ed97119e53807ef14e
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759339B2

Reaction notes

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