Borane;tetrahydrofuran → HCID 67079826, compound

HRID 655521Notes

Reaction equation

HRID 655521 reaction equation
B.O1CCCC1.[CH:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([CH2:17][C@@H:18]([NH2:22])[C:19](O)=[O:20])[CH:8]=1>O1CCCC1>[NH2:22][C@H:18]([CH2:17][C:9]1[CH:8]=[CH:7][CH:12]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:10]=1)[CH2:19][OH:20]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 7005132HCID 7005132, compound

Product 1

HCID 67079826HCID 67079826, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-tetrahydrofuran complex (1 M in tetrahydrofuran, 21.4 ml, 21.4 mmol) was added at 0° C. to a solution of D-3-trifluoromethylphenylalanine (2.00 g, 8.57 mmol) in tetrahydrofuran (45 ml). The reaction mixture was allowed to reach room temperature over 3 h, then partitioned between sat. aq. sodium carbonate solution and ethyl acetate. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; dichloromethane/methanol/25% aq. ammonia solution 90:10:0.25) afforded the title compound (1.58 g, 84%). Colorless oil, MS (ISP)=220.3 (M+H)+.

Workup

  1. custompartitioned between sat. aq. sodium carbonate solution and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-31cd31162f424775bf4e8ee5eaa1370c
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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