Tetrahydrofuran → HCID 68294110, compound

HRID 2279533Notes

Reaction equation

HRID 2279533 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@H:12]([OH:16])[CH2:13][C:14]#[N:15])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].C1COCC1>O>[NH2:15][CH2:14][CH2:13][C@@H:12]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([F:9])([F:10])[F:11])=[C:2]([F:1])[CH:3]=1)[OH:16]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 68294666HCID 68294666, compound

Product 1

HCID 68294110HCID 68294110, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 282 (0.5 g, 2.1 mmol) and THF (10 mL) was added BH3—SMe2 (2.1 mL, 4.3 mmol) and the reaction was stirred at 65° C. for 8 h. The reaction was poured into water and extracted with DCM. The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with EtOAc/MeOH/NH4OH (90/9/1) to afford 0.48 g (94%) of (S)-3-amino-1-(3-fluoro-4-(trifluoromethyl)phenyl)propan-1-ol (284).

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by SiO2 chromatography
  6. washeluting with EtOAc/MeOH/NH4OH (90/9/1)

Sources & evidence

ORD record
ord-6947094ee6384731a990d422d023b767
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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