Triethylamine → HCID 68504060, compound

HRID 1715406Notes

Reaction equation

HRID 1715406 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]1[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH:30]1([NH2:33])[CH2:32][CH2:31]1.[BH4-].[Na+].C([O-])(O)=O.[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:33][CH:30]2[CH2:32][CH2:31]2)[CH:14]=1)[CH2:8][CH:9]1[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 69828CyclopropylamineHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 86622956HCID 86622956, compound

Product 1

HCID 68504060HCID 68504060, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (4-chloro-3-formyl-benzyl)-cyclopropylmethyl-carbamic acid tert-butyl ester (1.00 g, 3.09 mmol), Et3N (0.646 mL, 4.64 mmol) and cyclopropylamine (0.325 mL, 4.64 mmol) in MeOH (10.5 mL) was heated to reflux for 4 h. The mixture was allowed to cool to rt, and NaBH4 (292 mg, 7.71 mmol) was added. The mixture was stirred for 1 h, and aq. sat. NaHCO3 was added. The mixture was extracted with EtOAc (2×). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (MeOH/CH2Cl2 1:49) yielded the title compound (535 mg, 48%). LC-MS: tR=0.81 min; ES+: 406.20.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. extractionThe mixture was extracted with EtOAc (2×)
  4. dry with materialextracts were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the crude by FC (MeOH/CH2Cl2 1:49)

Sources & evidence

ORD record
ord-ada5ea9a80084da8ba4192c01ee5c690
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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