Potassium Sodium Tartrate → HCID 57795370, compound

HRID 2099687Notes

Reaction equation

HRID 2099687 reaction equation
[NH:1]1[C:5]2([CH2:14][CH2:13][C:8]3([O:12][CH2:11][CH2:10][O:9]3)[CH2:7][CH2:6]2)[C:4](=O)[NH:3][C:2]1=[O:16].[H-].[H-].[H-].[H-].[Li+].[Al+3].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1>[NH:1]1[C:5]2([CH2:14][CH2:13][C:8]3([O:12][CH2:11][CH2:10][O:9]3)[CH2:7][CH2:6]2)[CH2:4][NH:3][C:2]1=[O:16]

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 167864459,12-Dioxa-1,3-diazadispiro[4.2.4.2]tetradecane-2,4-dioneHCID 21226445Aluminium lithium hydride

Product 1

HCID 57795370HCID 57795370, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 9,12-dioxa-1,3-diaza-dispiro[4.2.4.2]tetradecane-2,4-dione (9.64 g, 42.6 mmol) in 143 mL of dry THF was treated at 0° C. with a solution of LiAlH4 1M in THF (94.0 mL, 94.0 mmol). The resulting mixture was stirred overnight at room temperature under nitrogen. An aqueous saturated solution of Rochelle's salt was added. It was stirred for 3 h, extracted 4× with EtOAc and 3× with dichloromethane. Organic portions were combined and concentrated. The crude was purified by silica gel column chromatography using a gradient from 1% CH2Cl2:MeOH to 10% CH2Cl2:MeOH as eluent to afford 9,12-Dioxa-1,3-diaza-dispiro[4.2.4.2]tetradecan-2-one (5.20 g, 57%) as a white solid.

Workup

  1. stirringIt was stirred for 3 h
  2. extractionextracted 4× with EtOAc and 3× with dichloromethane
  3. concentrationconcentrated
  4. customThe crude was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0f733cab87ed4069ad62a486b8ca8dc8
Source dataset
uspto-grants-2009_08
Patent number
US07569600B2

Reaction notes

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