Diketene → HCID 178468084, compound

HRID 1055229Notes

Reaction equation

HRID 1055229 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][CH2:3]1.[CH2:9]=[C:10]1[O:14][C:12](=[O:13])[CH2:11]1>O1CCCC1>[OH:8][C@H:5]1[CH2:6][CH2:7][C@H:2]([NH:1][C:12](=[O:13])[CH2:11][C:10](=[O:14])[CH3:9])[CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 12661DiketeneHCID 178511715HCID 178511715, compound

Product 1

HCID 178468084HCID 178468084, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 28.8 g (0.25 mol) trans-4-aminocyclohexanol in 200 ml tetrahydrofuran was added dropwise to a solution of 20 g of diketene (0.24 mol) in 200 ml tetrahydrofuran at −5 to 0° C. After 1 h stirring at 0° C. no more starting material was detected by thin layer chromatography. The reaction mixture was evaporated and the residue is recrystallized from 200 ml of ethyl acetate. This gave 33.6 g (0.17 mol, 71% yield) of a colorless solid.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue is recrystallized from 200 ml of ethyl acetate

Sources & evidence

ORD record
ord-5e66b1c94368412880b84e787eb9b89f
Source dataset
uspto-grants-2016_07
Patent number
US09394324B2

Reaction notes

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