Water → HCID 69472417, compound

HRID 853777Notes

Reaction equation

HRID 853777 reaction equation
[C:1]1([C@H:7]2[NH:11][C@@H:10]([CH2:12][OH:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC.[CH3:21][Si:22](Cl)([CH3:24])[CH3:23].O>C(Cl)Cl>[C:1]1([C@H:7]2[CH2:8][CH2:9][C@@H:10]([CH2:12][O:13][Si:22]([CH3:24])([CH3:23])[CH3:21])[NH:11]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 69470953HCID 69470953, compound

Product 1

HCID 69472417HCID 69472417, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (2R,5S)-(5-phenyl-pyrrolidin-2-yl)-methanol (0.78 g, 4.4 mmol) in CH2Cl2 (7 mL) at 0° C. was added 0.72 mL (5.2 mmol, 1.2 eq) of Et3N followed by a slow addition of 0.66 mL (5.2 mmol, 1.2 eq) of TMSCl. The mixture was stirred at 0° C. for 45 min. Water (3 mL) was added to quench the reaction. The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (2 mL×2). The combined organic layer was dried (Na2SO4) and concentrated under vacuum to give 0.98 g (89%) of (2R,5S)-2-phenyl-5-trimethylsilanyloxymethyl-pyrrolidine as a yellow oil. 1H NMR (CDCl3, 300 MHz) δ 7.60–7.30 (5H, m), 4.30 (1H, m), 3.85 (2H, m), 3.50 (1H, m), 2.25 (1H, m), 2.05 (1H, m), 0.25 (9H, m).

Workup

  1. customto quench
  2. customthe reaction
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with CH2Cl2 (2 mL×2)
  5. dry with materialThe combined organic layer was dried (Na2SO4)
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b685767ea96a4ad6a4bf6089fb4a9b7d
Source dataset
uspto-grants-2007_08
Patent number
US07256186B2

Reaction notes

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