Trifluoroacetic acid → (2S,4R)-(4-Tritylsulfanyl-pyrrolidin-2-yl)-methanol

HRID 431834Notes

Reaction equation

HRID 431834 reaction equation
C(OC([N:8]1[CH2:12][C@H:11]([S:13][C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[CH2:33][OH:34])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:14]([S:13][C@H:11]1[CH2:12][NH:8][C@H:9]([CH2:33][OH:34])[CH2:10]1)([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11271474(2S,4R)-2-hydroxymethyl-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 11451661(2S,4R)-(4-Tritylsulfanyl-pyrrolidin-2-yl)-methanolYield 111.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 25.0 g (52.56 mmol) (2S,4R)-2-Hydroxymethyl-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester in 80 ml CH2Cl2 were added 40 ml TFA at 0° C., and the solution was stirred at RT over night. The solution was concentrated in vacuo, and the residue was redissolved in EtOAc, washed with sat. NaHCO3 solution, brine, and was dried over Na2SO4. 21.98 g (quant.) (2S,4R)-(4-Tritylsulfanyl-pyrrolidin-2-yl)-methanol were isolated as light brown foam.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionthe residue was redissolved in EtOAc
  3. washwashed with sat. NaHCO3 solution, brine
  4. dry with materialwas dried over Na2SO4

Sources & evidence

ORD record
ord-07d9f9abd693436fa9f50059e6d22007
Source dataset
uspto-grants-2003_12
Patent number
US06660738B2

Reaction notes

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