(R)-1-[3-(t-butyl-dimethyl-silanyloxy)-phenyl-sulfanylcarbonyl]-pyrrolidine-2-carboxylic acid ethyl ester → (R)-1-(3-Hydroxy-phenylsulfanylcarbonyl)-pyrrolidine-2-carboxylic acid ethyl ester

HRID 1994071Notes

Reaction equation

HRID 1994071 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11]([S:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][Si](C(C)(C)C)(C)C)[CH:15]=1)=[O:12])=[O:5])[CH3:2]>C1COCC1>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11]([S:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=1)=[O:12])=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 86605607(R)-1-[3-(t-butyl-dimethyl-silanyloxy)-phenyl-sulfanylcarbonyl]-pyrrolidine-2-carboxylic acid ethyl ester

Product 1

HCID 86605609(R)-1-(3-Hydroxy-phenylsulfanylcarbonyl)-pyrrolidine-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the title B compound, (R)-1-[3-(t-butyl-dimethyl-silanyloxy)-phenylsulfanyl-carbonyl]-pyrrolidine-2-carboxylic acid ethyl ester (1.5 g, 3.66 mmol) in a flask at RT, is added 1 M solution of n-tetrabutylammonium fluoride (14.6 mL, 14.6 mmol) in THF and the reaction is stirred for 4 h. The reaction mixture is concentrated at reduced pressure, diluted with ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated. The crude (R)-1-(3-hydroxy-phenylsulfanylcarbonyl)-pyrrolidine-2-carboxylic acid ethyl ester is used in the next step without further purification.

Workup

  1. concentrationThe reaction mixture is concentrated at reduced pressure
  2. additiondiluted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude (R)-1-(3-hydroxy-phenylsulfanylcarbonyl)-pyrrolidine-2-carboxylic acid ethyl ester is used in the next step without further purification

Sources & evidence

ORD record
ord-cac5f89088f14791a1e9311853ad7003
Source dataset
uspto-grants-2010_01
Patent number
US07652061B2

Reaction notes

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