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

HRID 1760718Notes

Reaction equation

HRID 1760718 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-c80dac76f5f64394a86211cef853d7b4
Source dataset
uspto-grants-2005_01
Patent number
US06844362B2

Reaction notes

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