Sodium Hydroxide → HCID 67148734, compound

HRID 2428141Notes

Reaction equation

HRID 2428141 reaction equation
[CH3:1][O:2][C:3](=[O:15])[NH:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([CH:13]=O)[CH:7]=1.[CH:16]1([NH2:19])[CH2:18][CH2:17]1.[BH4-].[Na+].[OH-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:15])[NH:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([CH2:13][NH:19][CH:16]2[CH2:18][CH2:17]2)[CH:7]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 69828CyclopropylamineHCID 4311764Sodium borohydrideHCID 86632363HCID 86632363, compound

Product 1

HCID 67148734HCID 67148734, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (4-chloro-3-formyl-benzyl)-carbamic acid methyl ester (3.22 g, 14.1 mmol) and cyclopropylamine (1.49 mL, 21.2 mmol) in MeOH (50 mL) was stirred at rt overnight. NaBH4 (1.07 g, 28.3 mmol) was added in portions, and the mixture was stirred at rt for 3 h. Aq. 1M NaOH (90 mL) was added, and the solvents were partially removed under reduced pressure. The aq. residue was extracted with EtOAc (3×). The combined org. extracts were washed with brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtOAc/heptane 1:1) yielded the title compound (3.24 g, 85%). LC-MS: tR=0.59 min; ES+: 310.31.

Workup

  1. stirringthe mixture was stirred at rt for 3 h
  2. customthe solvents were partially removed under reduced pressure
  3. extractionThe aq. residue was extracted with EtOAc (3×)
  4. washextracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure
  8. customPurification of the crude by FC (EtOAc/heptane 1:1)

Sources & evidence

ORD record
ord-c21299ad1d0d4196b4dc602b84f91efd
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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