Acetic Acid → HCID 178453946, compound

HRID 29760Notes

Reaction equation

HRID 29760 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([CH:14]=O)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O)(=O)C.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:16])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH:14]=[N:24][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 11020615rac-tert-butyl N-[(1r,4r)-4-formylcyclohexyl]carbamate

Product 1

HCID 178453946HCID 178453946, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (4-Formyl-cyclohexyl)-carbamic acid tert-butyl ester (3.80 g, 16.7 mmol), benzylamine (1.82 g, 16.7 mmol), acetic acid (0.01 g, 16.7 mmol) and anhydrous magnesium sulfate (4.01 g, 33.3 mmol) in methylene chloride (20 mL) was stirred for 5 days. The mixture was filtered through Celite and concentrated under reduced pressure to give trans-[4-(benzylimino-methyl)-cyclohexyl]-carbamic acid tert-butyl ester (5.10 g, 97%) as a 97:3 trans:cis mixture.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-67c0726d081f47c497c6dc117ec935da
Source dataset
uspto-grants-2008_09
Patent number
US07423012B2

Reaction notes

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