(2S,4R)-2-benzyloxymethyl-4-tert-butoxy-1-(naphthalene-2-sulfonyl)-pyrrolidine → (3R,5S)-5-benzyloxymethyl-1-(naphthalene-2-sulfonyl)-pyrrolidin-3-ol

HRID 458371Notes

Reaction equation

HRID 458371 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]1[CH2:14][C@@H:13]([O:15]C(C)(C)C)[CH2:12][N:11]1[S:20]([C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1)(=[O:22])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[CH2:1]([O:8][CH2:9][C@H:10]1[N:11]([S:20]([C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=2)(=[O:22])=[O:21])[CH2:12][C@H:13]([OH:15])[CH2:14]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 69433315(2S,4R)-2-benzyloxymethyl-4-tert-butoxy-1-(naphthalene-2-sulfonyl)-pyrrolidine

Product 1

HCID 69432400(3R,5S)-5-benzyloxymethyl-1-(naphthalene-2-sulfonyl)-pyrrolidin-3-olYield 82.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Trifluoroacetic acid (100 ml) was cooled to 0° C., then (2S,4R)-2-benzyloxymethyl-4-tert-butoxy-1-(naphthalene-2-sulfonyl)-pyrrolidine (7.0 g) was added in one portion. The reaction mixture was stirred for 3 h at the same temperature and then concentrated without heating under vacuum. The residue crystallized from Et2O/hexane to obtain (3R,5S)-5-benzyloxymethyl-1-(naphthalene-2-sulfonyl)-pyrrolidin-3-ol (5.07 g) as a colorless solid, mp 124–126° C., MS: 398 (MH+).

Workup

  1. concentrationconcentrated
  2. temperaturewithout heating under vacuum
  3. customThe residue crystallized from Et2O/hexane

Sources & evidence

ORD record
ord-5dbeed5425fe401f9f24bf8ab82f81a1
Source dataset
uspto-grants-2007_03
Patent number
US07189756B2

Reaction notes

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