Cyclopropylamine → HCID 86622952, compound

HRID 2428163Notes

Reaction equation

HRID 2428163 reaction equation
[C:1]([O:5][C:6](=[O:22])[N:7]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([CH:20]=O)[CH:14]=1)[CH2:8][CH:9]([F:11])[F:10])([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]([CH2:12][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)[CH2:8][CH:9]([F:11])[F:10])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 4311764Sodium borohydrideHCID 86622953HCID 86622953, compound

Product 1

HCID 86622952HCID 86622952, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(4-Chloro-3-formyl-benzyl)-(2,2-difluoro-ethyl)-carbamic acid tert-butyl ester (563 mg, 1.69 mmol) was dissolved in MeOH (18 mL). Cyclopropylamine (0.181 mL, 2.53 mmol) was added, and the mixture was heated to reflux for 4 h. The mixture was allowed to cool to rt, and NaBH4 (96 mg, 95.7 mg, 2.53 mmol) was added in portions. The mixture was stirred for 1 h, and the solvents were removed under reduced pressure. The residue was taken in EtOAc, and the mixture was washed with aq. sat. NaHCO3 (1×) and brine (1×). 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 (558 mg, 88%). LC-MS: tR=0.76 min; ES+: 375.15.

Workup

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

Sources & evidence

ORD record
ord-bd845ea012de4f4a8ab4b097a3a2f6e2
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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