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Thioanisole → Methyl (3s,7as)-6-benzyloxycarbonylamino-5-oxohexahydropyrrolizine-3-carboxylate

HRID 10424
Notes
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Reaction equation

HRID 10424 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:30]([O:32]C)=O)[CH2:13][C@H:14]1[N:18](C(OC(C)(C)C)=O)[C@H:17]([C:26]([O:28][CH3:29])=[O:27])[CH2:16][CH2:15]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(SC)C=CC=CC=1>FC(F)(F)C(O)=O>[CH2:1]([O:8][C:9]([NH:11][CH:12]1[CH2:13][C@H:14]2[N:18]([C@H:17]([C:26]([O:28][CH3:29])=[O:27])[CH2:16][CH2:15]2)[C:30]1=[O:32])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 7520ThioanisoleHCID 1317258971-Tert-butyl 2-methyl (2s,5s)-5-(2-benzyloxycarbonylamino-2-methoxycarbonylethyl)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 91509044Methyl (3s,7as)-6-benzyloxycarbonylamino-5-oxohexahydropyrrolizine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
95 °C

Procedure

1500 mg of 1-tert-butyl 2-methyl (2S,5S)-5-(2-benzyloxycarbonylamino-2-methoxycarbonylethyl)pyrrolidine-1,2-dicarboxylate were mixed with 0.2 ml of thioanisole. Then 10 ml of trifluoroacetic acid were added, and the mixture was stirred for 45 min. The solvents were then removed in vacuo, and the residue was taken up in 10 ml of pyridine. 1.1 ml of diisopropylethylamine were added, and the mixture was heated at 95° C. for 3 h. The solvents were removed in vacuo, and the residue was chromatographed on silica gel.

Workup

  1. customThe solvents were then removed in vacuo
  2. addition1.1 ml of diisopropylethylamine were added
  3. customThe solvents were removed in vacuo
  4. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-cb72a94ce0d34f9d96a25ac130802067
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07094800B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes