[(Z)-[1-amino-2-(8-phenyl-1,4-dioxaspiro[4.5]decan-8-yl)ethylidene]amino] acetate → 2-(8-Phenyl-1,4-dioxa-spiro[4.5]dec-8-yl)acetamidine acetic acid salt

HRID 2169302Notes

Reaction equation

HRID 2169302 reaction equation
[C:1]([O:4]/[N:5]=[C:6](\[NH2:24])/[CH2:7][C:8]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:17][CH2:16][C:11]2([O:15][CH2:14][CH2:13][O:12]2)[CH2:10][CH2:9]1)(=[O:3])[CH3:2]>CO.[Pd]>[C:1]([OH:4])(=[O:3])[CH3:2].[C:18]1([C:8]2([CH2:7][C:6]([NH2:24])=[NH:5])[CH2:9][CH2:10][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:16][CH2:17]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 1

HCID 90271666[(Z)-[1-amino-2-(8-phenyl-1,4-dioxaspiro[4.5]decan-8-yl)ethylidene]amino] acetate

Product 1

HCID 867259482-(8-Phenyl-1,4-dioxa-spiro[4.5]dec-8-yl)acetamidine acetic acid saltYield 88.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of (Z)-(1-amino-2-{8-phenyl-1,4-dioxaspiro[4.5]decan-8-yl}ethylidene)amino acetate (267) (1.4 g, 4.21 mmol) in methanol was added Pd—C (10%) under nitrogen atmosphere and the mixture was kept under a hydrogen atmosphere of balloon pressure at room temperature for 2 h (reaction was monitored by LC-MS). The reaction mixture was filtered and the filtrate was concentrated in vacuo to get a sticky mass which was triturated with diethyl ether to get pure 2-(8-phenyl-1,4-dioxa-spiro[4.5]dec-8-yl)acetamidine acetic acid salt (268) (1.25 g, 88.79%) as a white solid.

Workup

  1. custom(reaction was monitored by LC-MS)
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto get a sticky mass which
  5. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-a0eecf92da494256998647ea0a9416c2
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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