Potassium Carbonate → (S)-(+)-4-(2,3-Epoxypropoxy)carbazole

HRID 507334

Reaction equation

[OH:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:21]([C@@H:23]1[O:25][CH2:24]1)Cl>CC(O)C>[O:25]1[CH2:24][C@H:23]1[CH2:21][O:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 4-Hydroxycarbazole (10.98 g, 0.06 mole) dissolved in IPA (60 mL) was added K2CO3 (20.73 g, 0.15 mole), followed by (R)-(−)-epichlorohydrin (7 ml, 0.09 mole) and the reaction mixture was slowly heated to 80-90° C. and then refluxed for 5 hours. Subsequently the reaction mixture was cooled to room temperature, worked up and purified following the procedure similar to one described in step I for the synthesis of example 23, to afford the desired compound as a light brown colored solid (7.56 g, 53%).

Workup

temperaturerefluxed for 5 hours
temperatureSubsequently the reaction mixture was cooled to room temperature
custompurified
customdescribed in step I for the synthesis of example 23

Sources & evidence

ORD record: ord-1664a56bfa674a54a21f971ad01bac96
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786142B2

Linked notes

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