Borane;tetrahydrofuran → HCID 57826474, compound

HRID 1960976Notes

Reaction equation

HRID 1960976 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@H:9]([C:21](O)=[O:22])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]([F:20])([F:19])[F:18])=[O:7])([CH3:4])[CH3:3].B.C1COCC1>C1COCC1>[OH:22][CH2:21][C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:2]([CH3:3])([CH3:1])[CH3:4])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]([F:20])([F:19])[F:18]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 2761473Boc-2-(trifluoromethyl)-L-phenylalanine

Product 1

HCID 57826474HCID 57826474, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-{[(1,1-dimethylethyl)oxy]carbonyl}-2-(trifluoromethyl)-L-phenylalanine (5 g, 15 mmol) in THF (75 mL) at 0° C. stirred was added BH3-THF (45 mL, 45 mmol-1M in THF). After 12 h, the reaction was quenched with AcOH:MeOH (1:5, 24 mL) and partitioned between saturated aqueous NaHCO3 and DCM. The aqueous phase was then extracted several times with DCM. The combined organic fractions were dried over Na2SO4 and used directly (4.2 g, 88%): LCMS (ES) m/e 320 (M+H)+.

Workup

  1. customthe reaction was quenched with AcOH:MeOH (1:5, 24 mL)
  2. custompartitioned between saturated aqueous NaHCO3 and DCM
  3. extractionThe aqueous phase was then extracted several times with DCM
  4. dry with materialThe combined organic fractions were dried over Na2SO4

Sources & evidence

ORD record
ord-17d463c6396a4646ac0783e30e7ed42f
Source dataset
uspto-grants-2013_04
Patent number
US08410158B2

Reaction notes

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