2-Cyclohexylacetaldehyde → HCID 54575451, compound

HRID 1746095Notes

Reaction equation

HRID 1746095 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C@@H:13]2[CH2:15][C@H:14]2[NH2:16])=[CH:9][CH:8]=1.[CH:20]1([CH2:26][CH:27]=O)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.[BH4-].[Na+]>ClCCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C@@H:13]2[CH2:15][C@H:14]2[NH:16][CH2:27][CH2:26][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 3166272-CyclohexylacetaldehydeHCID 4311764Sodium borohydrideHCID 67452233HCID 67452233, compound

Product 1

HCID 54575451HCID 54575451, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (Trans)-2-(4-(3-bromobenzyloxy)phenyl)cyclopropanamine (2 g, 6.2 mmol) and 2-cyclohexylacetaldehyde (790 mg, 6.2 mmol) in DCE (20 mL) sodium triacetoxy borohydrate (2.3 g, 2 equiv) was added slowly at 0° C. and stirred for 20 h. After completion, the reaction mixture was evaporated. The residue was dissolved in Methanol (15 mL) and NaBH4 (627 mg, 3 equiv) was added slowly at 0° C. to the reaction mixture and stirred for 3 h. After completion, the reaction mixture was poured into ice water (50 mL) and extracted with EtOAc (2×50 mL). The combined organic layers were washed with brine (50 mL) and dried over anhydrous Na2SO4, filtered and evaporated. The crude residue was purified by flash column chromatography by using EtOAc: Pet ether to get (Trans)-2-(4-(3-bromobenzyloxy) phenyl)-N-(2-cyclohexylethyl)cyclopropane amine (500 mg, 21%) as a pale yellow liquid.

Workup

  1. customAfter completion, the reaction mixture was evaporated
  2. dissolutionThe residue was dissolved in Methanol (15 mL)
  3. stirringstirred for 3 h
  4. extractionextracted with EtOAc (2×50 mL)
  5. washThe combined organic layers were washed with brine (50 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-d914130eaebf44f6a763a404d7851d18
Source dataset
uspto-grants-2015_10
Patent number
US09149447B2

Reaction notes

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