Triethylborane → (2R,4S)-2-Methyl-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 238989Notes

Reaction equation

HRID 238989 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:10][C@H:9]1[CH2:19]OS(C)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li].CN([BH3-])C.C(B(CC)CC)C>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:10][C@H:9]1[CH3:19])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7357TriethylboraneHCID 58002926(2S,4S)-2-Methanesulfonyloxymethyl-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 131731184CID 131731184

Product 1

HCID 58002924(2R,4S)-2-Methyl-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl esterYield 67.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.4 g of (2S,4S)-2-Methanesulfonyloxymethyl-4-phenyl-pyrrolidine-1-carboxylic acid tert-butyl ester (9.56 mmol) were dissolved in 50 ml tetrahydrofurane. After addition of 15.1 ml lithium-dimethylaminoborohydride (14.34 mmol; 1 M in tetrahydrofurane), 1.93 ml triethylborane (1 M in tetrahydrofurane) were added and the reaction mixture stirred under reflux for 20 min. Standard workup gave 2.7 g of crude product which was purified via silica gel chromatography using a ISCO Companion instrument, yielding 1.69 g of purified product.

Workup

  1. additionwere added
  2. temperatureunder reflux for 20 min
  3. customStandard workup gave 2.7 g of crude product which
  4. customwas purified via silica gel chromatography

Sources & evidence

ORD record
ord-7fb7bb9bcbb5407cb1376fa8e004c492
Source dataset
uspto-grants-2014_02
Patent number
US08642642B2

Reaction notes

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