Cyclopropylamine → HCID 67148693, compound

HRID 2428119Notes

Reaction equation

HRID 2428119 reaction equation
[C:1]([O:5][C:6](=[O:22])[N:7]([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([CH:20]=O)[CH:14]=1)[CH:8]1[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH:23]1([NH2:26])[CH2:25][CH2:24]1.[BH4-].[Na+]>CO>[C:1]([O:5][C:6](=[O:22])[N:7]([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([CH2:20][NH:26][CH:23]2[CH2:25][CH2:24]2)[CH:14]=1)[CH:8]1[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 4311764Sodium borohydrideHCID 86622971HCID 86622971, compound

Product 1

HCID 67148693HCID 67148693, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of [2-(4-chloro-3-formyl-phenyl)-ethyl]-cyclopropyl-carbamic acid tert-butyl ester (1.32 g, 4.08 mmol) and cyclopropylamine (0.438 mL, 6.26 mmol) in MeOH (41 mL) was heated to reflux for 4 h. The mixture was allowed to cool to rt, and NaBH4 (232 mg, 6.14 mmol) was added in portions. The mixture was stirred for 1 h, and the solvents were removed under reduced pressure. EtOAc (100 mL) was added, and the mixture was washed with aq. sat. NaHCO3 and brine. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (CH2Cl2/MeOH 95:5) yielded the title compound (883 mg, 59%). LC-MS: tR=0.82 min; ES+: 365.38.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. customthe solvents were removed under reduced pressure
  4. additionEtOAc (100 mL) was added
  5. washthe mixture was washed with aq. sat. NaHCO3 and brine
  6. dry with materiallayer was dried over MgSO4
  7. filtrationfiltered
  8. customthe solvents were removed under reduced pressure
  9. customPurification of the crude by FC (CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-775c68e0e7f54ebb86588f5aa47f15d7
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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