Sodium Hydroxide → 2-Fluoro-alpha-methylbenzenemethanol
Reaction equation
O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20](=[O:22])[CH3:21].[OH-].[Na+]>C1C=[N+]([C@@H]2O[C@H](COP(OP(OC[C@H]3O[C@@H](N4C5N=CN=C(N)C=5N=C4)[C@H](OP(O)(O)=O)[C@@H]3O)(O)=O)(O)=O)[C@@H](O)[C@H]2O)C=C(C(N)=O)C=1>[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]([OH:22])[CH3:21]Participants
Conditions
- Temperature
- 30 °C
Procedure
The culture of the recombinant Escherichia coli HB101(pNTRGG1) as obtained in Example 9 was subjected to ultrasonic cell disruption using SONIFIRE 250 (product of BRANSON). To 100 ml of this cell disruption fluid, there were added 15 g of glucose, 5 g of 1-(2′-fluorophenyl)ethanone and 15 mg of NADP. This reaction mixture was stirred at 30° C. for 24 hours while adjusting the pH to 6.5 with 5 M sodium hydroxide. After completion of the reaction, this reaction mixture was extracted with ethyl acetate, the solvent was then removed, and the extract was distilled (54° C./1 mm Hg) to obtain 4.1 g of 1-(2′-fluorophenyl)ethanol as a colorless oil. Its specific rotation showed a value of [α] (25,D)=−45.3 (c=0.794, methanol) and it was the S form with an optical purity of 99.9% ee.
Workup
- customas obtained in Example 9
- customAfter completion of the reaction
- extractionthis reaction mixture was extracted with ethyl acetate
- customthe solvent was then removed
- distillationthe extract was distilled (54° C./1 mm Hg)
Sources & evidence
- ORD record
- ord-4940833c70a04eceb2ecab3ccc522ebd
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07332312B2
Reaction notes
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