Cyclopropylamine → HCID 86622952, compound

HRID 1715397Notes

Reaction equation

HRID 1715397 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

A mixture of (4-chloro-3-formyl-benzyl)-(2,2-difluoro-ethyl)-carbamic acid tert-butyl ester (563 mg, 1.69 mmol) and cyclopropylamine (0.180 mL, 2.52 mmol) in MeOH (18 mL) was heated to reflux for 4 h. The mixture was allowed to cool to rt. NaBH4 (96 mg, 2.53 mmol) was added by portions, and the reaction was stirred for 1 h. The solvents were removed under reduced pressure, and the resulting oil was diluted with EtOAc. 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 (558 mg, 88%). LC-MS: tR=0.76 min; ES+: 375.17.

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
  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-8f0f5118cafe4fd28e09a4e544c0ca40
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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