Trimethylphosphine → tert-Butyl 3-[3-(1-aminoethyl)-5-chloro-6-fluoro-2-methoxyphenyl]azetidine-1-carboxylate

HRID 510948Notes

Reaction equation

HRID 510948 reaction equation
[N:1]([CH:4]([C:6]1[C:7]([O:25][CH3:26])=[C:8]([CH:14]2[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:15]2)[C:9]([F:13])=[C:10]([Cl:12])[CH:11]=1)[CH3:5])=[N+]=[N-].CP(C)C>C1COCC1.O>[NH2:1][CH:4]([C:6]1[C:7]([O:25][CH3:26])=[C:8]([CH:14]2[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH2:15]2)[C:9]([F:13])=[C:10]([Cl:12])[CH:11]=1)[CH3:5]

Participants

5

Reactant 2

HCID 68983TrimethylphosphineHCID 86666862tert-Butyl 3-[3-(1-azidoethyl)-5-chloro-6-fluoro-2-methoxyphenyl]azetidine-1-carboxylate

Product 1

HCID 86666863tert-Butyl 3-[3-(1-aminoethyl)-5-chloro-6-fluoro-2-methoxyphenyl]azetidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of tert-butyl 3-[3-(1-azidoethyl)-5-chloro-6-fluoro-2-methoxyphenyl]azetidine-1-carboxylate (0.084 g, 0.22 mmol) in THF (1 mL)/water (0.2 mL) was added 1.0 M trimethylphosphine in THF (0.33 mL, 0.33 mmol) at room temperature and the mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with water and extracted with EtOAc. The combined organic layers were dried over MgSO4 and concentrated to give the desired product to be used in the next step without further purification.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9c521b5b10c94cc7b778ca719b10dade
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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