Formaldehyde → HCID 25143668, compound

HRID 1931840Notes

Reaction equation

HRID 1931840 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:14])[CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.[CH2:15]=O>C(O)=O>[F:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:14])[CH2:13][CH2:12][N:11]([CH3:15])[CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 63585886HCID 63585886, compound

Product 1

HCID 25143668HCID 25143668, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Preparation according to Example 11: Enantiomer E1 of 3-(3,5-difluorophenyl)-pyrrolidin-3-ol (0.18 g, 0.92 mmol), formic acid (2.6 mL), aqueous formaldehyde (40%, 2.45 mL). Purification on a Biotage Isolute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine, 4:1) and by flash chromatography on silica gel (ethyl acetate/methanol, 10:1). Yield: 0.125 g. [α]D=+19.8° (methanol). The amine was converted to the oxalic acid salt and recrystallized from ethanol/diethyl ether/diisopropyl ether: M.p. 150° C.; MS m/z (relative intensity, 70 eV) 213 (M+, 14), 57 (bp), 58 (31), 113 (13), 127 (11), 141 (10).

Workup

  1. customPreparation
  2. customPurification
  3. washon a Biotage Isolute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine, 4:1)
  4. customrecrystallized from ethanol/diethyl ether/diisopropyl ether

Sources & evidence

ORD record
ord-af1f312a0d5f409fb2406a397ff84c2d
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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