Sodium Hydroxide → 3-Fluoro-4-(pyrrolidin-1-ylmethyl)phenol

HRID 1035199Notes

Reaction equation

HRID 1035199 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(Cl)Cl.O>[F:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH2:4][N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 31268PyrrolidineHCID 5872462-Fluoro-4-hydroxybenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 580430903-Fluoro-4-(pyrrolidin-1-ylmethyl)phenolYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-fluoro-4-hydroxybenzaldehyde (0.42 g, 3.00 mmol) in DCM (15 mL) was added pyrrolidine (0.26 g, 3.60 mmol). After stirring for 20 min, sodium triacetoxyborohydride (0.76 g, 3.60 mmol) was added and the reaction mixture was stirred overnight. The mixture was then diluted with DCM and transferred to a separatory funnel. Water was added, basified to pH 9-10 with a 0.1 M solution of NaOH and extracted 6 times with DCM. The organic layer was dried (phase separator) and concentrated in vacuo. There was obtained 0.55 g (94%) of 31A as a solid. 1H NMR (500 MHz, CDCl3): δ 1.85 (s, 4H), 2.70 (s, 4H), 3.60 (s, 2H), 6.25 (m, 2H), 7.00 (m, 1H).

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. customtransferred to a separatory funnel
  3. extractionextracted 6 times with DCM
  4. customThe organic layer was dried (phase separator)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-00605c1be65c41d8ba76a4a296f25344
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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