Potassium Sodium Tartrate → HCID 57795370, compound

HRID 1694516Notes

Reaction equation

HRID 1694516 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-1da5330c2f4b4f4793b8f367319348a3
Source dataset
uspto-grants-2012_04
Patent number
US08158675B2

Reaction notes

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