Cyclopropylamine → HCID 68508703, compound

HRID 1715417Notes

Reaction equation

HRID 1715417 reaction equation
[C:1]([O:5][C:6](=[O:19])[N:7]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([CH:17]=O)[CH:11]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH:20]1([NH2:23])[CH2:22][CH2:21]1.[BH4-].[Na+]>CO>[C:1]([O:5][C:6](=[O:19])[N:7]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([CH2:17][NH:23][CH:20]2[CH2:22][CH2:21]2)[CH:11]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 4311764Sodium borohydrideHCID 86622959HCID 86622959, compound

Product 1

HCID 68508703HCID 68508703, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (4-chloro-3-formyl-benzyl)-methyl-carbamic acid tert-butyl ester (95 mg, 0.335 mmol) and cyclopropylamine (0.036 mL, 0.50 mmol) in MeOH (3.30 mL) was heated to reflux for 4 h. The mixture was allowed to cool to rt, and NaBH4 (19 mg, 0.50 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 (20 mL), and this 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 residue by FC (CH2Cl2/MeOH 90:10) yielded the title compound (81 mg, 75%). LC-MS: tR=0.73 min; ES+: 366.20.

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 (20 mL)
  5. washthis 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 residue by FC (CH2Cl2/MeOH 90:10)

Sources & evidence

ORD record
ord-a8f7c4bf7074426489ef89a178bce8fc
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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