Tributylstannane → HCID 18316587, compound

HRID 275811Notes

Reaction equation

HRID 275811 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([SnH:17]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH3:16].[C:26]([O:30][C:31]([N:33]1[CH2:37][CH2:36][C:35](=[O:38])[CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]>C1COCC1>[C:26]([O:30][C:31]([N:33]1[CH2:37][CH2:36][C:35]([OH:38])([Sn:17]([CH2:13][CH2:14][CH2:15][CH3:16])([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:34]1)=[O:32])([CH3:29])([CH3:27])[CH3:28]

Participants

6

Reactant 4

HCID 5948TributylstannaneHCID 7912DiisopropylamineHCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 178418339Butyllithium

Product 1

HCID 18316587HCID 18316587, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

Diisopropylamine (25.2 mL, 0.18 mol) in anhydrous THF (500 mL) is cooled to 0° C. and n-butyllithium (112.5 mL of a 1.6 M solution in THF, 0.18 mol) is added dropwise over 20 minutes to the cooled solution. The reaction mixture is stirred for an additional 15 minutes at 0° C. and then tri-n-butyltinhydride (48.4 mL, 0.18 mol) is added dropwise over 30 minutes. The reaction mixture is then stirred for one hour and then cooled to −78° C. N-(t-butoxycarbonyl)-3-pyrrolidone (0.15 mol) in THF (500 mL) is then added dropwise to the cooled solution over one hour. After addition is complete, the reaction is stirred for 2 hours at −78° C. and then quenched with buffer (pH 6). The mixture is extracted with ethyl acetate, the organic extracts are combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue is purified by flash chromatrography (5% ethyl acetate/hexane to provide 1-(t-butoxycarbonyl)-3-hydroxy-3-tributylstannyl pyrrolidine.

Workup

  1. stirringThe reaction mixture is then stirred for one hour
  2. temperaturecooled to −78° C
  3. additionAfter addition
  4. stirringthe reaction is stirred for 2 hours at −78° C.
  5. customquenched with buffer (pH 6)
  6. extractionThe mixture is extracted with ethyl acetate
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe residue is purified by flash chromatrography (5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-d2012c57cd584e6a8740d1505f338222
Source dataset
uspto-grants-2002_03
Patent number
US06353008B1

Reaction notes

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