(4-Phenyl-but-3-ynyl)-carbamic acid tert-butyl ester → cis-4-Phenyl-but-3-enylamine

HRID 6725

Reaction equation

HRID 6725 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][C:10]#[C:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(C)(C)C>N1C=CC=CC=1.[Pd]>[C:12]1(/[CH:11]=[CH:10]\[CH2:9][CH2:8][NH2:7])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 23544319(4-Phenyl-but-3-ynyl)-carbamic acid tert-butyl ester

Product 1

HCID 12594566cis-4-Phenyl-but-3-enylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1049PyridineSolvent

Procedure

A suspension of palladium on barium sulfate (15 mg) was stirred for 15 min in 1 mL pyridine. (4-phenyl-but-3-ynyl)-carbamic acid tert-butyl ester (66 mg) was added and the solution was purged with hydrogen then stirred for 1 h under a hydrogen-filled balloon. The solution was diluted with ethyl acetate (10 ml) and washed 3 times with 1 N hydrochloric acid (10 ml). The ethyl acetate layer was dried over sodium sulfate and filtered. The filtrate was evaporated and the resulting residue (54 mg) is primarily cis-(4-phenyl-but-3-enyl)-carbamic acid tert-butyl ester along with (4-phenyl-but-3-ynyl)-carbamic acid tert-butyl ester, 4-phenylbutylamine, and trans-(4-phenyl-but-3-enyl)-carbamic acid tert-butyl ester. The combined minor products constitute ˜20% of the crude material. The tert-butoxycarbonyl group of the desired product was removed by Procedure P to give cis-4-phenyl-but-3-enylamine, which was used in subsequent transformations without further purification.

Workup

  1. customthe solution was purged with hydrogen
  2. additionfilled balloon
  3. additionThe solution was diluted with ethyl acetate (10 ml)
  4. washwashed 3 times with 1 N hydrochloric acid (10 ml)
  5. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated
  8. customThe tert-butoxycarbonyl group of the desired product was removed by Procedure P

Sources & evidence

ORD record
ord-1ba07cbda9804effb51403d0992a3d41
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Linked notes

Loading…