Formaldehyde → HCID 25143668, compound

HRID 1931835Notes

Reaction equation

HRID 1931835 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 E2 of 3-(3,5-difluorophenyl)-pyrrolidin-3-ol (0.29 g, 1.45 mmol), formic acid (3.8 mL), aqueous formaldehyde (40%, 3.4 mL). 65° C. for 5 h. Purification by flash chromatography on silica gel (ethyl acetate/methanol, 10:1). Yield: 0.19 g. [α]D=−22.8° (methanol). The amine was converted to the oxalic acid salt and recrystallized from ethanol/diethyl ether/diisopropyl ether: M.p. 134-135° C.; MS m/z (relative intensity, 70 eV) 213 (M+, 15), 57.1 (bp), 58.1 (31), 113 (13), 127 (11), 141 (11).

Workup

  1. customPreparation
  2. customPurification by flash chromatography on silica gel (ethyl acetate/methanol, 10:1)
  3. customrecrystallized from ethanol/diethyl ether/diisopropyl ether

Sources & evidence

ORD record
ord-5e4fe352e19c46dc881a054aca2dcb7d
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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