Boron trifluoride etherate → HCID 59799035, compound

HRID 1013110Notes

Reaction equation

HRID 1013110 reaction equation
[C:1]([C:4]1[CH:20]=[CH:19][C:7]2[CH2:8][CH2:9][N:10]([C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[CH2:11][CH2:12][C:6]=2[C:5]=1[OH:21])(=O)[CH3:2].B(F)(F)F.CCOCC.C([BH3-])#N.[Na+].C([SiH](CC)CC)C>C1COCC1>[CH2:1]([C:4]1[CH:20]=[CH:19][C:7]2[CH2:8][CH2:9][N:10]([C:13](=[O:18])[C:14]([F:17])([F:15])[F:16])[CH2:11][CH2:12][C:6]=2[C:5]=1[OH:21])[CH3:2]

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 59799040HCID 59799040, compound

Product 1

HCID 59799035HCID 59799035, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Under nitrogen dissolve 7-acetyl-6-hydroxy-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (1.0 g, 3.32 mmol) in anhydrous THF (100 mL). Cool the solution to 0° C., add boron trifluoride diethyl etherate (3.4 mL, 26.6 mmol) and sodium cyanoborohydride (836 mg, 13.3 mmol). Remove the ice bath and stir for 5 h at RT. Dilute with EtOAc and wash with 0.1 N HCl. Separate the organic layer, dry (sodium sulfate) and concentrate. MS (ES): m/z=302 [M−H]. Mix the residue with trifluoroacetic acid (40 mL) and anhydrous DCM (50 mL) under nitrogen. Cool to 0° C. in an ice bath and add triethylsilane (3.5 mL, 21.9 mmol). After 15 min, remove the ice bath and stir at RT for 16 h. Concentrate and purify (silica gel chromatography, eluting with 10:90 EtOAc:hexanes to give the title compound (698 mg, 73%).

Workup

  1. customRemove the ice bath
  2. additionDilute with EtOAc
  3. washwash with 0.1 N HCl
  4. customSeparate the organic layer
  5. dry with materialdry (sodium sulfate)
  6. concentrationconcentrate
  7. additionMix the residue with trifluoroacetic acid (40 mL) and anhydrous DCM (50 mL) under nitrogen
  8. temperatureCool to 0° C. in an ice bath
  9. waitAfter 15 min
  10. customremove the ice bath
  11. stirringstir at RT for 16 h
  12. concentrationConcentrate
  13. custompurify (silica gel chromatography
  14. washeluting with 10:90 EtOAc

Sources & evidence

ORD record
ord-2adb70b387044bdc92f6c3e384827aa6
Source dataset
uspto-grants-2011_07
Patent number
US07981882B2

Reaction notes

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