Triethylamine → HCID 68502068, compound

HRID 1715414Notes

Reaction equation

HRID 1715414 reaction equation
[C:1]([O:5][C:6](=[O:20])[N:7]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([CH:18]=O)[CH:12]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH:28]1([NH2:31])[CH2:30][CH2:29]1.[BH4-].[Na+].C([O-])(O)=O.[Na+]>CO>[C:1]([O:5][C:6](=[O:20])[N:7]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([CH2:18][NH:31][CH:28]2[CH2:30][CH2:29]2)[CH:12]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 69828CyclopropylamineHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 86622958HCID 86622958, compound

Product 1

HCID 68502068HCID 68502068, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of [2-(4-chloro-3-formyl-phenyl)-ethyl]-methyl-carbamic acid tert-butyl ester (325 mg, 1.09 mmol), Et3N (0.228 mL, 1.64 mmol) and cyclopropylamine (0.115 mL, 1.64 mmol) in MeOH (3.66 mL) was heated to reflux for 4 h. The mixture was allowed to cool to rt, and NaBH4 (103 mg, 2.73 mmol) was added. The mixture was stirred for 1 h at rt, and aq. sat. NaHCO3 was added. The mixture was extracted with EtOAc several times. The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC yielded the title compound (186 mg, 50%). LC-MS: tR=0.79 min; ES+: 339.39.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. extractionThe mixture was extracted with EtOAc several times
  4. dry with materialextracts were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the crude by FC

Sources & evidence

ORD record
ord-fd722ea5e14c4ebd9f207f179c16b93e
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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