Lithium tri-s-butylborohydride → HCID 131733492, compound

HRID 2279601Notes

Reaction equation

HRID 2279601 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH:7]2[C:11](=[O:12])[CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]2)=[CH:4][C:3]=1[F:22].CCC(C)[BH-](C(C)CC)C(C)CC.[Li+]>C1COCC1>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C@H:7]2[C@@H:11]([OH:12])[CH2:10][N:9]([C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14])[CH2:8]2)=[CH:4][C:3]=1[F:22]

Participants

4

Reactant 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 68295207HCID 68295207, compound

Product 1

HCID 131733492HCID 131733492, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 416 (1.6 g, 4.9 mmol) and anhydrous THF (50 mL) cooled to −78° C. was added dropwise L-selectride (1.0 M, 15 mL) and then the reaction was stirred at −78° C. for 3 h. The reaction was quenched with H2O (30 mL). The mixture was extracted with EtOAc (3×100 mL) and the extract was washed with brine (3×30 mL). The organic phases were dried (Na2SO4), filtered and concentrated. LC-MS indicated about 9:1 of two isomers. The residue was purified by reverse phase column chromatography using a MeCN/5% aqueous NH4OH (0 to 35%) to afford 0.56 g (35%) of cis-(±)-tert-butyl 3-(4-chloro-3-fluorophenoxy)-4-hydroxy-pyrrolidine-1-carboxylate (418). LC-MS (ESI) m/z 276 (M+H-56).

Workup

  1. customThe reaction was quenched with H2O (30 mL)
  2. extractionThe mixture was extracted with EtOAc (3×100 mL)
  3. washthe extract was washed with brine (3×30 mL)
  4. dry with materialThe organic phases were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by reverse phase column chromatography

Sources & evidence

ORD record
ord-189079c4ea2847d89f564df25cd94afe
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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