Water → HCID 22864761, compound

HRID 1078708Notes

Reaction equation

HRID 1078708 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@H:9]1[CH2:21][CH:22]=[O:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+].O.S([O-])(O)(=O)=O.[K+].O1CCC[CH2:34]1>>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@H:9]1[CH2:21][CH:22]([OH:23])[CH3:34])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 516920Potassium bisulfateHCID 10807344HCID 10807344, compound

Product 1

HCID 22864761HCID 22864761, compoundYield 51%

Procedure

To a solution of 1.6M methyllithium-ether solution (5.5 ml, 8.8 mmol) in tetrahydrofuran (20 ml) was added (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(formylmethyl)pyrrolidine (1.67 g, 4.86 mmol) under a nitrogen atmosphere at -70° C., and the mixture was stirred for 2 h at the same temperature. To the mixture was added saturated aqueous ammonium chloride (3 ml) below -70° C., and then the mixture was warmed at room temperature. The reaction mixture was poured into a mixture of water (200 ml) and 1N aqueous potassium hydrogensulfate (20 ml), and extracted with ethyl acetate (3×50 ml). The combined organic layer was washed successively with water and saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate. The solvent was removed in vacuo, and the residue was subjected to silica gel column chromatography (heptane-ethyl acetate) to give (2R,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(2-hydroxypropyl)pyrrolidine diastereomer A (890 mg, yield: 51%) and diastereomer B (350 mg, yield: 20%).

Workup

  1. extractionextracted with ethyl acetate (3×50 ml)
  2. washThe combined organic layer was washed successively with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1e65e24590fd44d3a0d1ef549c6ee5a6
Source dataset
uspto-grants-1996_08
Patent number
US05550121

Reaction notes

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