Potassium Sodium Tartrate → HCID 57795370, compound

HRID 1190065Notes

Reaction equation

HRID 1190065 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-80b7e46c3786480bb2a8fd53ff53cb6a
Source dataset
uspto-grants-2014_03
Patent number
US08674118B2

Reaction notes

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