Hydrochloric Acid → HCID 117778748, compound

HRID 2201762Notes

Reaction equation

HRID 2201762 reaction equation
Cl.C([NH:9][C@@H:10]([C@@H:44]1[C@H:48]([CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62])[O:47]C(C)(C)[O:45]1)[CH2:11][O:12][C@H:13]1[C@H:19]([O:20]CC2C=CC=CC=2)[C@@H:18]([O:28]CC2C=CC=CC=2)[C@@H:17]([O:36]CC2C=CC=CC=2)[CH:16]=[CH:15][CH2:14]1)C1C=CC=CC=1.C1CCCCC=1>CO.C(Cl)(Cl)Cl.[Pd]>[NH2:9][C@@H:10]([C@@H:44]([OH:45])[C@@H:48]([OH:47])[CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62])[CH2:11][O:12][C@@H:13]1[CH2:14][CH2:15][CH2:16][C@H:17]([OH:36])[C@H:18]([OH:28])[C@H:19]1[OH:20]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8079CyclohexeneHCID 117778423HCID 117778423, compound

Product 1

HCID 117778748HCID 117778748, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A 1M solution of HCl (150 μL, 0.15 mmol) and Pd—C (10% wt, 32 mg, 0.03 mmol) were added to a solution of ether 71 (130 mg, 0.15 mmol) and cyclohexene (2 mL) in MeOH (10 mL) and heated under reflux. After stirring overnight the reaction mixture was cooled to rt and diluted with a 5:1 solution of CHCl3:MeOH, before being filtered thought a bed of celite. The filtrate was concentrated under reduced pressure to provide the crude amine 72, which was used directly in the next step.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. filtrationMeOH, before being filtered
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d37810fb4e1c478c84a1293cc42b767c
Source dataset
uspto-grants-2016_06
Patent number
US09365496B2

Reaction notes

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