Formaldehyde → 3-(3,4-Difluorophenyl)-1-methylpyrrolidin-3-ol

HRID 1931806Notes

Reaction equation

HRID 1931806 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]=[CH:6][C:7]=1[F:8].C=O.[C:17](O)(=O)/C=C/C(O)=O>C(O)=O>[F:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:14])[CH2:13][CH2:12][N:11]([CH3:17])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 444972Fumaric AcidHCID 635869723-(3,4-Difluorophenyl)pyrrolidin-3-ol

Product 1

HCID 251436663-(3,4-Difluorophenyl)-1-methylpyrrolidin-3-ol

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Preparation according to Example 26: 3-(3,4-difluorophenyl)-pyrrolidin-3-ol (1.32 g, 6.63 mmol), formic acid (19.2 mL), aqueous formaldehyde (40%, 17.2 mL). 60° C. for 24 h. Yield: 0.83 g. The amine was converted to the fumaric acid salt and recrystallized from methanol/diethyl ether/diisopropyl ether: M.p. 164-166° C.; MS m/z (relative intensity, 70 eV) 213 (M+, 7), 141 (10), 113 (10), 58 (43), 57 (bp).

Workup

  1. customPreparation
  2. customrecrystallized from methanol/diethyl ether/diisopropyl ether

Sources & evidence

ORD record
ord-9e40390b2b1d4048ba4bf34394c262d6
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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