Lithiumtriethylborohydride → 1,1-Dimethylethyl (2R,3S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-(hydroxymethyl)-1-pyrrolidinecarboxylate

HRID 1864699Notes

Reaction equation

HRID 1864699 reaction equation
C[O:2][C:3]([C@@H:5]1[C@@H:9]([O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH2:8][CH2:7][N:6]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=O.C([BH-](CC)CC)C.[Li+]>C1COCC1>[C:21]([O:20][C:18]([N:6]1[CH2:7][CH2:8][C@H:9]([O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[C@H:5]1[CH2:3][OH:2])=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 23664628LithiumtriethylborohydrideHCID 58841066Methyl (2S,3S)-1-Boc-3-[(tert-butyldimethylsilyl)oxy]pyrrolidine-2-carboxylate

Product 1

HCID 109256021,1-Dimethylethyl (2R,3S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-(hydroxymethyl)-1-pyrrolidinecarboxylateYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of compound 4A (4.30 g, 12.0 mmol) in THF (75 mL) at −78° C. under nitrogen was added dropwise a solution of 1.0 M lithium triethylborohydride in tetrahydrofuran (60.0 mL, 60.0 mmol). The reaction was allowed to warm to rt and was stirred for 4 h. The reaction was then quenched by pouring over ice (150 g) and stirring for 30 min. The product was extracted into EtOAc and was washed with saturated aqueous NaHCO3. The organic layer was dried over MgSO4, filtered and concentrated. Purification via flash chromatography (silica gel, 0-15% EtOAc in hexane) provided compound 5A (3.30 g).

Workup

  1. customThe reaction was then quenched
  2. additionby pouring over ice (150 g)
  3. stirringstirring for 30 min
  4. extractionThe product was extracted into EtOAc
  5. washwas washed with saturated aqueous NaHCO3
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification via flash chromatography (silica gel, 0-15% EtOAc in hexane)

Sources & evidence

ORD record
ord-157fc2d0d72e4bd99d249181326afa90
Source dataset
uspto-grants-2009_12
Patent number
US07625923B2

Reaction notes

Loading…