(Trifluoromethyl)trimethylsilane → HCID 66624992, compound
Reaction equation
[CH3:1][C@H:2]1[NH:6][C@@H:5]([CH:7]=[O:8])[CH2:4][CH2:3]1.[C:9]([Si](C)(C)C)([F:12])([F:11])[F:10]>>[F:10][C:9]([F:12])([F:11])[CH:7]([C@H:5]1[CH2:4][CH2:3][C@@H:2]([CH3:1])[NH:6]1)[OH:8]Participants
3
Procedure
2,2,2-trifluoro-1-((2R,5R)-5-methylpyrrolidin-2-yl)ethanol (Compound 2, Scheme I, R3=methyl) is prepared by oxidation of ((2R,5R)-5-methylpyrrolidin-2-yl)methanol (Compound 4, Scheme I, R3=methyl) to afford the resulting aldehyde, (2R,5R)-5-methylpyrrolidine-2-carbaldehyde (see e.g., Smith et al., March's Advanced Organic Chemistry, 6th ed., Wiley, N.J., 2007, p. 1715-1728). The resulting aldehyde is reacted with CF3-TMS (trimethyl(trifluoromethyl)silane) to afford 2,2,2-trifluoro-1-((2R,5R)-5-methylpyrrolidin-2-yl)ethanol (see e.g., Prakash et al., J. Am. Chem. Soc. 111: 393, 1989).
Sources & evidence
- ORD record
- ord-4e09fdd9fe1c45b781241f0580f85908
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09139520B2
Reaction notes
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