(Trifluoromethyl)trimethylsilane → HCID 66625104, compound
Reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][C@@H:2]1[CH:3]=[O:4].[C:8]([Si](C)(C)C)([F:11])([F:10])[F:9]>>[F:9][C:8]([F:11])([F:10])[C@@H:3]([CH:2]1[CH2:5][CH2:6][CH2:7][NH:1]1)[OH:4]Participants
3
Procedure
Compounds of Structures 2 and 4 are prepared from D-proline or D-pyroglutamic acid. For example, (R)-2,2,2-trifluoro-1-(pyrrolidin-2-yl)ethanol (Compound 2, Scheme I, R3=hydrogen) is prepared by oxidation of D-prolinol (Compound 4, Scheme I, R3=hydrogen) to afford D-prolinaldehyde (see e.g., Smith et al., March's Advanced Organic Chemistry, 6th ed., Wiley, N.J., 2007, p. 1715-1728). The resulting D-prolinaldehyde is reacted with CF3-TMS (trimethyl(trifluoromethyl)-silane) to afford the (R)-2,2,2-trifluoro-1-(pyrrolidin-2-yl)ethanol (see e.g., Prakash et al., J. Am. Chem. Soc. 111: 393, 1989).
Sources & evidence
- ORD record
- ord-dbc68bd17d9d4038b63f029aa84f0500
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08748633B2
Reaction notes
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