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Water → t-Butyl 2-(2-(3-cyano-5-fluorophenyl)-4-((methylamino)methyl)phenoxy)acetate

HRID 68603
Notes
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Reaction equation

HRID 68603 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:10]2[CH:24]=[C:23]([CH:25]=O)[CH:22]=[CH:21][C:11]=2[O:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:6]=[C:7]([F:9])[CH:8]=1)#[N:2].[CH3:27][NH2:28].[BH4-].[Na+].O>C1COCC1.CO>[C:1]([C:3]1[CH:4]=[C:5]([C:10]2[CH:24]=[C:23]([CH2:25][NH:28][CH3:27])[CH:22]=[CH:21][C:11]=2[O:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:6]=[C:7]([F:9])[CH:8]=1)#[N:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 86681838t-Butyl 2-(2-(3-cyano-5-fluorophenyl)-4-formylphenoxy)acetate

Product 1

HCID 67528259t-Butyl 2-(2-(3-cyano-5-fluorophenyl)-4-((methylamino)methyl)phenoxy)acetate

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

A solution of t-butyl 2-(2-(3-cyano-5-fluorophenyl)-4-formylphenoxy)acetate (21) (120 g, 338 mmol) and MeNH2 (203 mL of a 2M solution in THF, 405 mmol) in methanol (300 mL) was stirred at room temperature for 2 h. Sodium borohydride (12 g, 316 mmol) was added, and the resulting mixture was stirred at room temperature for additional 2 h. Water (30 mL) was added and the MeOH was removed in vacuo. The resulting solution was extracted with EA (3×), and the combined organic layers were dried over Na2SO4, filtered, and concentrated. The crude product t-butyl 2-(2-(3-cyano-5-fluorophenyl)-4-((methylamino)methyl)phenoxy)acetate (22) was used in the next reaction without further purification.

Workup

  1. customthe MeOH was removed in vacuo
  2. extractionThe resulting solution was extracted with EA (3×)
  3. dry with materialthe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product t-butyl 2-(2-(3-cyano-5-fluorophenyl)-4-((methylamino)methyl)phenoxy)acetate (22) was used in the next reaction without further purification

Sources & evidence

ORD record
ord-225107d194c64ed38ad4e067db21140b
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822467B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes