(Dimethyl sulfide)trihydroboron → HCID 66971281, compound

HRID 1361310Notes

Reaction equation

HRID 1361310 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][C@H:10]([N:13]([CH:21]2[CH2:26][CH2:25][C:24]([CH3:28])([CH3:27])[CH2:23][CH2:22]2)[C:14](=O)[C:15]([CH3:19])([CH3:18])[CH2:16][OH:17])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].B.CSC>C1COCC1>[C:1]([N:8]1[CH2:12][CH2:11][CH:10]([N:13]([CH:21]2[CH2:26][CH2:25][C:24]([CH3:28])([CH3:27])[CH2:23][CH2:22]2)[CH2:14][C:15]([CH3:19])([CH3:18])[CH2:16][OH:17])[CH2:9]1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 66971267HCID 66971267, compound

Product 1

HCID 66971281HCID 66971281, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (3S)-1-Boc-3-[(4,4-dimethylcyclohexyl)(3-hydroxy-2,2-dimethylpropanoyl)amino]pyrrolidine (210 mg, 0.53 mmol) prepared in Step B of Example A8 in THF was added dropwise borane-methylsulfide complex (in THF, 2.0M, 0.4 ml, 0.8 mmol), and stirred at 80° C. for 3 h. After the reaction finished, the solvent was concentrated in vacuo, water added, extracted with EtOAc. The organic layer was dried over MgSO4, concentrated in vacuo, and purified by column chromatography (eluent: DCM/MeOH=9/1) to give the title compound (140 mg, 75%).

Workup

  1. concentrationthe solvent was concentrated in vacuo, water
  2. additionadded
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography (eluent: DCM/MeOH=9/1)

Sources & evidence

ORD record
ord-e44ee05590764abdb06e1a83e1458ba7
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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