Triphenylphosphine → Tert-butyl (S)-3-(acetylthio)pyrrolidine-1-carboxylate

HRID 404735Notes

Reaction equation

HRID 404735 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10](O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[C:45]([OH:48])(=[S:47])[CH3:46]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([S:47][C:45](=[O:48])[CH3:46])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylateHCID 178418634HCID 178418634, compound

Product 1

HCID 59560788Tert-butyl (S)-3-(acetylthio)pyrrolidine-1-carboxylateYield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3 g (16 mmol) (R)-3-Hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester and 4.63 g Triphenylphosphine were dissolved in 70 ml THF. Over a period of 10 min 2.8 ml (17.6 mmol) Diethylazodicarboxylate were added at 0° C. After 10 min 1.26 ml (17.6 mmol) Thioacetic acid was added and the mixture was allowed to come to RT and stirring was continued for 18 h. After evaporation the residue was purified over silica gel (heptane to 20% ethyl acetate in heptane) to give 3.5 g of the expected compound.

Workup

  1. customto come to RT
  2. customAfter evaporation the residue
  3. customwas purified over silica gel (heptane to 20% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-81447a4e6093467a9a378ac16ca6ea99
Source dataset
uspto-grants-2014_06
Patent number
US08748614B2

Reaction notes

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