Lithium borohydride → HCID 66970919, compound

HRID 1361314Notes

Reaction equation

HRID 1361314 reaction equation
[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]([CH:20]2[CH2:25][CH2:24][C:23]([CH3:27])([CH3:26])[CH2:22][CH2:21]2)[C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:10][C@@H:9]1[CH2:28]OS(C)(=O)=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Li+].[BH4-]>C1COCC1>[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]([CH:20]2[CH2:25][CH2:24][C:23]([CH3:27])([CH3:26])[CH2:22][CH2:21]2)[C:14](=[O:19])[C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:10][C@H:9]1[CH3:28])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 86636642HCID 86636642, compound

Product 1

HCID 66970919HCID 66970919, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of BOC-(2R,4S)-4-[(4,4-dimethylcyclohexyl)(2,2-dimethylpropanoyl)amino]-2-{[(methylsulfonyl)oxy]methyl}pyrrolidine (580 mg, 1.19 mmol) prepared in Step B in THF (5 ml) was added dropwise LiBH4 (77 mg, 3.57 mmol) at 70° C. The solution was stirred at 70° C. for 5 h, concentrated in vacuo, and extracted with EtOAC. The organic extracts were washed with a saturated NaHCO3 aqueous solution and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by column chromatography (eluent: EtOAc:Hex=1/4) to give the title compound (258 mg, 53%).

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with EtOAC
  3. washThe organic extracts were washed with a saturated NaHCO3 aqueous solution and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (eluent: EtOAc:Hex=1/4)

Sources & evidence

ORD record
ord-75e785300bf240fda57e324cdcbc7d2f
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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