Lithium triethylborohydride → HCID 86709987, compound

HRID 537252Notes

Reaction equation

HRID 537252 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-03659e0ad9ab4155a3d2c1a9074ccd20
Source dataset
uspto-grants-2014_10
Patent number
US08859774B2

Reaction notes

Loading…