Formaldehyde → HCID 57891811, compound

HRID 1820678Notes

Reaction equation

HRID 1820678 reaction equation
[CH:1]1([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:5][CH:4]=[CH:3][CH2:2]1.C=O.Cl.[OH:16][NH:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH2:25](N(CC)CC)C>C1(C)C=CC=CC=1.CCO>[C:19]1([CH2:18][N:17]2[CH2:25][C@H:4]3[CH2:5][C@H:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C@H:3]3[O:16]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 8471TriethylamineHCID 11332622N-benzylhydroxylamine hydrochlorideHCID 20802387HCID 20802387, compound

Product 1

HCID 57891811HCID 57891811, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of 1,1-dimethylethyl 3-cyclopentene-1-carboxylate (8.4 g, 50.0 mmole) [JACS, 1983, 105, 2435-2439] in toluene (150 mL) and EtOH (75 mL) was added paraformaldehyde (11.0 g, 250 mmole), N-hydroxybenzylamine hydrochloride (11.8 g, 75 mmole) and triethylamine (10.4 mL, 75 mmole). After 24 hours at 80° C., the reaction solution was concentrated under vacuum and redissolved in hexanes/EtOAc, 4:1 (200 mL) and filtered. The organic solution was concentrated and then purified on silica (hexanes/EtOAc, 4:1) to give the title compound (13.0 g, 86%) as a light yellow oil: LC-MS (ES) m/e 304 (M+H)+.

Workup

  1. concentrationthe reaction solution was concentrated under vacuum
  2. dissolutionredissolved in hexanes/EtOAc
  3. filtration4:1 (200 mL) and filtered
  4. concentrationThe organic solution was concentrated
  5. custompurified on silica (hexanes/EtOAc, 4:1)

Sources & evidence

ORD record
ord-d0a80b1d125640beb02a2c942009474e
Source dataset
uspto-grants-2009_10
Patent number
US07605169B2

Reaction notes

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