Hydrochloric Acid → HCID 66654055, compound

HRID 588227Notes

Reaction equation

HRID 588227 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=2[C:21]([F:24])([F:23])[F:22])[O:11][CH2:10][C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.C1COCC1.Cl>C1COCC1>[CH2:1]([N:8]1[CH2:9][CH2:10][O:11][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=2[C:21]([F:24])([F:22])[F:23])[CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 66653985HCID 66653985, compound

Product 1

HCID 66654055HCID 66654055, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 4-benzyl-6-(4-hydroxy-2-trifluoromethyl-phenyl)-morpholin-3-one (26.18 g; 67.3 mmol) in THF (600 mL) was added dropwise BH3.THF in THF (235.4 mL; 1.00 mold; 235.4 mmol), at 0° C. The resulting mixture was stirred for 1 hour at 0° C. and thereafter 18 hours at RT. Subsequently, 1M aqueous HCl (550 mL) was added and the mixture stirred overnight at RT. The resulting mixture was partitioned between EtOAc and 2M aqueous NaOH (350 mL), the organic layers was dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, CH2Cl2/MeOH 98:2) to afford 4-(4-benzyl-morpholin-2-yl)-3-trifluoromethyl-phenol

Workup

  1. customat 0° C
  2. custom18 hours
  3. customat RT
  4. stirringthe mixture stirred overnight at RT
  5. customThe resulting mixture was partitioned between EtOAc and 2M aqueous NaOH (350 mL)
  6. dry with materialthe organic layers was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography (SiO2, CH2Cl2/MeOH 98:2)

Sources & evidence

ORD record
ord-9c95645f0f4b40d687265505c89459c0
Source dataset
uspto-grants-2016_01
Patent number
US09227960B2

Reaction notes

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