Water → HCID 59536348, compound

HRID 445297Notes

Reaction equation

HRID 445297 reaction equation
[BH4-].[Na+].O.C(=O)(O)[O-].[Na+].[F:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16]([C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=1)=[N:15][CH2:14][CH2:13]2>C(OCC)(=O)C>[F:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]([C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:28])([F:27])[F:29])=[CH:22][CH:21]=1)[NH:15][CH2:14][CH2:13]2

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 59536270HCID 59536270, compound2×

Product 1

HCID 59536348HCID 59536348, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-fluoro-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline (2.6 g, 8.9 mmol) in methanol (50 mL) from step 2 was cooled to 0° C. and sodium borohydride (1.0 g, 2.7 mmol) was added in small portions over 5 min and the reaction mixture was stirred at RT for 16 h. The reaction was quenched with ethyl acetate (20 mL) and concentrated to yield a reddish-yellow residue which was taken up in ethyl acetate (100 mL), water (30 mL), and saturated sodium bicarbonate (30 mL). After stirring for 15 min, it was transferred to a separatory funnel, the organic layer was separated, dried over anhydrous sodium sulfate, and concentrated to yield the crude product. The crude product was purified by silica gel chromatography (20-30% EtOAc in hexanes) to give 6-fluoro-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline as a pale-yellow solid. MS (ESI pos. ion) m/z: 296 (M+H).

Workup

  1. customThe reaction was quenched with ethyl acetate (20 mL)
  2. concentrationconcentrated
  3. customto yield a reddish-yellow residue which
  4. stirringAfter stirring for 15 min
  5. customit was transferred to a separatory funnel
  6. customthe organic layer was separated
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customto yield the crude product
  10. customThe crude product was purified by silica gel chromatography (20-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-88cf7a56bc2146fdbd922a4082c78111
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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