Formaldehyde → 3-(3-Chloro-2-fluorophenyl)-1-methylpyrrolidin-3-ol

HRID 1931809

Reaction equation

HRID 1931809 reaction equation
[Cl:1][C:2]1[C:3]([F:14])=[C:4]([C:8]2([OH:13])[CH2:12][CH2:11][NH:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[CH2:15]=O>C(O)=O>[Cl:1][C:2]1[C:3]([F:14])=[C:4]([C:8]2([OH:13])[CH2:12][CH2:11][N:10]([CH3:15])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 685157443-(3-Chloro-2-fluorophenyl)pyrrolidin-3-ol

Product 1

HCID 251436693-(3-Chloro-2-fluorophenyl)-1-methylpyrrolidin-3-ol

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Preparation according to Example 26: 3-(3-chloro-2-fluorophenyl)-pyrrolidin-3-ol (0.6 g, 2.78 mmol), formic acid (8.1 mL), aqueous formaldehyde (40%, 7.2 mL). Purification by flash chromatography on silica gel (ethyl acetate/methanol, 2:8 to 3:8) and by HPLC on Waters OBD C18, 5 μm (MeOH/33 mM NH3, 20:80 to 100:0). Yield: 0.3 g. The amine was converted to the fumaric acid salt and evaporated to a solid residue: MS m/z (relative intensity, 70 eV) 229 (M+, 10), 157 (8), 129 (5), 58 (28), 57 (bp).

Workup

  1. customPreparation
  2. customPurification by flash chromatography on silica gel (ethyl acetate/methanol, 2:8 to 3:8)
  3. customevaporated to a solid residue

Sources & evidence

ORD record
ord-792d9c734f844d88ba48fb38943b9254
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Linked notes

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