Cyclopropylamine → HCID 67148536, compound

HRID 2428108Notes

Reaction equation

HRID 2428108 reaction equation
[C:1]([O:5][C:6](=[O:21])[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([CH:19]=O)[CH:13]=1)[CH:8]1[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH:22]1([NH2:25])[CH2:24][CH2:23]1.[BH4-].[Na+]>CO>[C:1]([O:5][C:6](=[O:21])[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([CH2:19][NH:25][CH:22]2[CH2:24][CH2:23]2)[CH:13]=1)[CH:8]1[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 4311764Sodium borohydrideHCID 86622969HCID 86622969, compound

Product 1

HCID 67148536HCID 67148536, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (4-chloro-3-formyl-benzyl)-cyclopropyl-carbamic acid tert-butyl ester (563 mg, 1.82 mmol) and cyclopropylamine (0.195 mL, 2.73 mmol) in MeOH (18 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 in portions. The mixture was stirred for 1 h, and the solvents were removed under reduced pressure. The resulting oil was diluted with EtOAc (100 mL), and the resulting 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 (343 mg, 54%). LC-MS: tR=0.78 min; ES+: 351.39.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. customthe solvents were removed under reduced pressure
  4. additionThe resulting oil was diluted with EtOAc (100 mL)
  5. washthe resulting 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-5e4eddafa6be486f84accaf43dd85ddf
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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