Water → 3-(3,5-Difluorophenyl)-3-methoxy-1-methyl pyrrolidine

HRID 575948Notes

Reaction equation

HRID 575948 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2([O:14][CH3:15])[CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.O.[CH2:17](OCC)C>C(O)=O.C=O>[F:1][C:2]1[CH:3]=[C:4]([C:9]2([O:14][CH3:15])[CH2:13][CH2:12][N:11]([CH3:17])[CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 3283Diethyl EtherHCID 199358743-(3,5-Difluorophenyl)-3-methoxypyrrolidine

Product 1

HCID 462192243-(3,5-Difluorophenyl)-3-methoxy-1-methyl pyrrolidine

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 712FormaldehydeSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of (+)-3-(3,5-difluorophenyl)-3-methoxypyrrolidine (0.02 g, 0.094 mmol) in formic acid (1 ml) and formaldehyde (37% solution in water, 1 ml) was heated at 85° C. for 5 h. The mixture was allowed to reach ambient temperature, water (5 ml) and diethyl ether was added, the phases were separated and the aqueous phase was basified by the addition of aqueous sodium hydroxide (5M). The aqueous phase was extracted twice with ethyl acetate, the combined organic phases was dried (Na2SO4) and evaporated to give the crude product which was diluted in methanol and analyzed by GCMS. MS m/z (relative intensity, 70 eV) 227 (M+, 5), 212 (29), 197 (25), 141 (42), 57 (bp).

Workup

  1. customto reach ambient temperature
  2. customthe phases were separated
  3. additionthe aqueous phase was basified by the addition of aqueous sodium hydroxide (5M)
  4. extractionThe aqueous phase was extracted twice with ethyl acetate
  5. dry with materialthe combined organic phases was dried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-b64bf6cf7f2a481a90b3038812099b02
Source dataset
uspto-grants-2015_05
Patent number
US09035073B2

Reaction notes

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