Cyclopropylamine → HCID 118307103, compound

HRID 921229Notes

Reaction equation

HRID 921229 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[CH3:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[C:8]([O:14][C@H:15]([CH2:17][CH:18]=[CH2:19])[CH3:16])[CH:7]=1.[BH4-].[Na+]>CO>[CH3:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][NH:4][CH:1]2[CH2:3][CH2:2]2)=[C:8]([O:14][C@H:15]([CH2:17][CH:18]=[CH2:19])[CH3:16])[CH:7]=1

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 4311764Sodium borohydrideHCID 118307095HCID 118307095, compound

Product 1

HCID 118307103HCID 118307103, compoundYield 12.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of cyclopropanamine (40.0 mg, 0.700 mmol), (S)-4-methyl-2-(pent-4-en-2-yloxy)benzaldehyde (130 mg, 0.636 mmol) in MeOH (5 mL) was stirred at rt for 0.5 h. Sodium borohydride (12.04 mg, 0.318 mmol) was then added and the reaction was stirred at rt for 2 h. It was then quenched with water, extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by biotage, eluting with 20% EtOAc/hexane to isolate (S)—N-(4-methyl-2-(pent-4-en-2-yloxy)benzyl)cyclopropanamine (20 mg, 0.082 mmol, 12.81% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.12 (d, J=7.8 Hz, 1H), 6.77-6.67 (m, 2H), 5.90 (ddt, J=17.2, 10.2, 7.1 Hz, 1H), 5.20-5.07 (m, 2H), 4.51 (sxt, J=6.0 Hz, 1H), 3.86-3.69 (m, 2H), 2.60-2.39 (m, 2H), 2.34 (s, 3H), 2.12-2.02 (m, 1H), 1.36 (d, J=6.1 Hz, 3H), 0.48-0.32 (m, 4H).

Workup

  1. stirringthe reaction was stirred at rt for 2 h
  2. customIt was then quenched with water
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by biotage
  8. washeluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-738c560b6d9d40a684d41b6dfec127e0
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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