Triethylamine → HCID 86610759, compound

HRID 225956Notes

Reaction equation

HRID 225956 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:3]1.C(N(CC)CC)C.[CH3:26][C:27]([Si:30](Cl)([CH3:32])[CH3:31])([CH3:29])[CH3:28]>ClCCl.CN(C1C=CN=CC=1)C.O>[Si:30]([O:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[C@H:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:3]1)([C:27]([CH3:29])([CH3:28])[CH3:26])([CH3:32])[CH3:31]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 12709318HCID 12709318, compound

Product 1

HCID 86610759HCID 86610759, compoundYield 98.6%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-tert-butyl 2-ethyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate (100 g, 0.38 mol) in dry dichloromethane (1.51) at 25° C. was added DMAP (47 g, 0.38 mol), followed by triethylamine (39 g, 0.38 mol). To the above reaction mixture was added TBDMSCl (64 g, 0.42 mol) dissolved in dry dichloromethane (200 ml) drop-wise over a period of 45 min. After stirring at RT for 20 h, the reaction mixture was diluted with water and separated the organic layer. The organic layer was washed with 5% aq. citric acid, brine and dried over Na2SO4. The solvent was removed under vacuum to give 1-tert-butyl 2-ethyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}pyrrolidine-1,2-dicarboxylate (140 g) as a colorless liquid. Yield: 97%

Workup

  1. customseparated the organic layer
  2. washThe organic layer was washed with 5% aq. citric acid, brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-b41feabea3cc4b9a9a775809ca174547
Source dataset
uspto-grants-2009_07
Patent number
US07557136B2

Reaction notes

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