Hydrochloric Acid → Methyl 5-((2R)-2-{[(1R)-1-phenylethyl]amino]propyl)-1H-indole-2-carboxylate

HRID 722773Notes

Reaction equation

HRID 722773 reaction equation
[C:1]1([C@H:7]([NH:9][C@H:10]([CH3:32])[CH2:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17](C(OC(C)(C)C)=O)[C:16]([C:28]([O:30][CH3:31])=[O:29])=[CH:15]3)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>CO>[C:1]1([C@H:7]([NH:9][C@H:10]([CH3:32])[CH2:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16]([C:28]([O:30][CH3:31])=[O:29])=[CH:15]3)[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 599792771-tert-butyl 2-methyl 5-((2R)-2-{[(1R)-1-phenylethyl]amino}propyl)-1H-indole-1,2-dicarboxylate

Product 1

HCID 59979291Methyl 5-((2R)-2-{[(1R)-1-phenylethyl]amino]propyl)-1H-indole-2-carboxylateYield 59.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-tert-butyl 2-methyl 5-((2R)-2-{[(1R)-1-phenylethyl]amino}propyl)-1H-indole-1,2-dicarboxylate (Preparation 16, 20.48 g, 46.9 mmol) was treated with 4M hydrogen chloride in methanol and the resulting solution left to stir at room temperature for 16 hours and then heated at 50° C. for a further 2 hours. The solvent was removed in vacuo to give a solid which was crystallised from a mixture of methanol (125 ml) and diisopropylether (50 ml) to give the title compound as a colourless crystalline solid (9.34 g, d.e.>98% as determined by 1H NMR).

Workup

  1. waitthe resulting solution left
  2. temperatureheated at 50° C. for a further 2 hours
  3. customThe solvent was removed in vacuo
  4. customto give a solid which
  5. customwas crystallised from a mixture of methanol (125 ml) and diisopropylether (50 ml)

Sources & evidence

ORD record
ord-2d9ae81fd1c7400199a28c22b51347ad
Source dataset
uspto-grants-2006_11
Patent number
US07138527B2

Reaction notes

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