Water → HCID 59536617, compound

HRID 1922169Notes

Reaction equation

HRID 1922169 reaction equation
[OH:1][CH:2]([C@H:6]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]1)[CH2:3][CH:4]=[CH2:5].[N+](=[CH2:20])=[N-].O>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:14]([O:13][C:11]([N:8]1[CH2:9][CH2:10][C@H:6]([CH:2]([OH:1])[CH2:3][CH:4]2[CH2:20][CH2:5]2)[CH2:7]1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 962WaterHCID 9550DiazomethaneHCID 59536652HCID 59536652, compound

Product 1

HCID 59536617HCID 59536617, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Add palladium (II) acetate (50.0 mg; 0.22 mmol) to a stirred solution of (3S)-tert-butyl 3-(1-hydroxybut-3-enyl)pyrrolidine-1-carboxylate (S-mix) (3.0 g, 12.43 mmol) and freshly prepared diazomethane (50 mL, about 23.8 mmol in diethyl ether) in THF (20 mL) under nitrogen at 0° C. (Caution: vigorous gas evolution). Stir at 0° C. for 10 minutes. Warm to room temperature, pour into water and extract with ethyl acetate (3×). Wash the combined organics with water and brine. Dry (MgSO4), filter and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with 0-100% ethyl acetate in hexane to afford 2.9 g (91%) of the title compound. MS (m/z)=200.0 (M−55)

Workup

  1. temperatureWarm to room temperature
  2. extractionextract with ethyl acetate (3×)
  3. washWash the combined organics with water and brine
  4. dry with materialDry (MgSO4)
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. washeluting with 0-100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-ee172b0521ae4f3486581a652f5a4e7d
Source dataset
uspto-grants-2012_05
Patent number
US08173821B2

Reaction notes

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