Lithium triethylborohydride → HCID 86709987, compound

HRID 920625Notes

Reaction equation

HRID 920625 reaction equation
[Li+].[B-](CC)(CC)CC.[F:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:20]3[CH:21]=[C:22]4[C@:27]([C:29](OC)=[O:30])([CH2:28][C:19]=3[CH:18]=[N:17]2)[CH2:26][N:25]([S:33]([C:36]2[CH:37]=[C:38]([CH3:42])[CH:39]=[CH:40][CH:41]=2)(=[O:35])=[O:34])[CH2:24][CH2:23]4)=[CH:12][CH:11]=1>O1CCCC1>[F:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:20]3[CH:21]=[C:22]4[C@:27]([CH2:29][OH:30])([CH2:28][C:19]=3[CH:18]=[N:17]2)[CH2:26][N:25]([S:33]([C:36]2[CH:37]=[C:38]([CH3:42])[CH:39]=[CH:40][CH:41]=2)(=[O:35])=[O:34])[CH2:24][CH2:23]4)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 23712863Lithium triethylborohydrideHCID 86709988HCID 86709988, compound

Product 1

HCID 86709987HCID 86709987, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Superhydride (1M solution in tetrahydrofuran, 43.2 ml, 43.2 mmol) was added slowly to a solution of (R)-methyl 1-(4-fluorophenyl)-6-(m-tolylsulfonyl)-4,4a,5,6,7,8-hexahydro-1H-pyrazolo[3,4-g]isoquinoline-4a-carboxylate (5.2 g, 10.80 mmol) in tetrahydrofuran (100 mL) at 0° C. and stirred for 2 hours. The reaction was quenched with ammonium chloride solution (aqueous, 100 mL) and ethyl acetate (100 mL) was added. The phases were separated and the organic phase was washed with brine (100 mL), dried (sodium sulphate) and solvent removed to give a yellow oil. The crude product was purified by chromatography on silica gel (gradient: 0-80% ethyl acetate in isohexane) to afford (R)-(1-(4-fluorophenyl)-6-(m-tolylsulfonyl)-4,4a,5,6,7,8-hexahydro-1H-pyrazolo[3,4-g]isoquinolin-4a-yl)methanol (4.45 g) as a white solid. LCMS (Method F, ES-API): RT 2.36 min, m+H=454.

Workup

  1. customThe reaction was quenched with ammonium chloride solution (aqueous, 100 mL) and ethyl acetate (100 mL)
  2. additionwas added
  3. customThe phases were separated
  4. washthe organic phase was washed with brine (100 mL)
  5. dry with materialdried (sodium sulphate) and solvent
  6. customremoved
  7. customto give a yellow oil
  8. customThe crude product was purified by chromatography on silica gel (gradient: 0-80% ethyl acetate in isohexane)

Sources & evidence

ORD record
ord-81cd49e14ebd4a26920716234d0833ce
Source dataset
uspto-grants-2016_03
Patent number
US09273047B2

Reaction notes

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