Acetic Acid → HCID 118939095, compound

HRID 524003Notes

Reaction equation

HRID 524003 reaction equation
Cl.[CH3:2][O:3][C:4]([C:6]1[C:7]2[CH2:8][CH2:9][NH:10][CH2:11][C:12]=2[CH:13]=[CH:14][CH:15]=1)=[O:5].[C:16]([O:20][C:21](=[O:33])[NH:22][C@H:23]([C:25]1[CH:30]=[CH:29][C:28]([CH:31]=O)=[CH:27][CH:26]=1)[CH3:24])([CH3:19])([CH3:18])[CH3:17].CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[CH3:2][O:3][C:4]([C:6]1[C:7]2[CH2:8][CH2:9][N:10]([CH2:31][C:28]3[CH:27]=[CH:26][C:25]([C@@H:23]([NH:22][C:21]([O:20][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:33])[CH3:24])=[CH:30][CH:29]=3)[CH2:11][C:12]=2[CH:13]=[CH:14][CH:15]=1)=[O:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 44607840Methyl 1,2,3,4-tetrahydroisoquinoline-5-carboxylate--hydrogen chloride (1/1)HCID 89479126HCID 89479126, compound

Product 1

HCID 118939095HCID 118939095, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 600 mg (2.64 mmol) 1,2,3,4-tetrahydro-isoquinoline-5-carboxylic acid methyl ester hydrochloride and 657 mg (2.64 mmol) [(S)-1-(4-formyl-phenyl)-ethyl]-carbamic acid tert-butyl ester (example II) in 5 mL THF are added 452 μL (7.91 mmol) AcOH and the mixture is stirred at r.t. for 10 min. After that time, the resulting mixture is cooled to 0° C., 838 mg (3.95 mmol) sodium triacetoxyborohydride are added and the reaction mixture is stirred at r.t. for 2 h. The reaction is quenched by the addition of 500 μl water and purified by HPLC (ACN/H2O/NH3).

Workup

  1. temperatureAfter that time, the resulting mixture is cooled to 0° C.
  2. stirringthe reaction mixture is stirred at r.t. for 2 h
  3. customThe reaction is quenched by the addition of 500 μl water
  4. custompurified by HPLC (ACN/H2O/NH3)

Sources & evidence

ORD record
ord-ef1e7375efff4329951676a80a910bfe
Source dataset
uspto-grants-2016_05
Patent number
US09340510B2

Reaction notes

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