Sodium sulfate decahydrate → 5-(N-methyl-3-tert-butoxycarbonylaminopropyl)-1,3-bis-(hydroxymethyl)-benzene

HRID 1695309Notes

Reaction equation

HRID 1695309 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[C:10]([CH2:12][CH2:13][CH2:14][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH3:16])[CH:9]=[C:8]([C:24](OCC)=[O:25])[CH:7]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.C(OCC)C>[CH3:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:13][CH2:12][C:10]1[CH:9]=[C:8]([CH2:24][OH:25])[CH:7]=[C:6]([CH2:4][OH:3])[CH:11]=1

Participants

6

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 671447525-(N-methyl-3-tert-butoxycarbonylaminopropyl)-benzene-1,3-dicarboxylic acid diethyl ester

Product 1

HCID 671449785-(N-methyl-3-tert-butoxycarbonylaminopropyl)-1,3-bis-(hydroxymethyl)-benzeneYield 85%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cooled solution (−5° C.) of 5-(N-methyl-3-tert-butoxycarbonylaminopropyl)-benzene-1,3-dicarboxylic acid diethyl ester (100 mg) in tetrahydrofuran (2 mL) was slowly added a 1M solution of lithium aluminium hydride in diethyl ether (0.55 mL). 10 minutes after the end of the addition, sodium sulfate decahydrate was added until gas evolution ceased. The solid was filtered off, washed twice with ethyl acetate and the combined organic solutions were concentrated in vacuo to give 5-(N-methyl-3-tert-butoxycarbonylaminopropyl)-1,3-bis-(hydroxymethyl)-benzene (66.8 mg) as a viscous oil:

Workup

  1. additionwas added until gas evolution
  2. filtrationThe solid was filtered off
  3. washwashed twice with ethyl acetate
  4. concentrationthe combined organic solutions were concentrated in vacuo

Sources & evidence

ORD record
ord-5035a29e85df44ed954797fb79eb3b62
Source dataset
uspto-grants-2012_04
Patent number
US08163736B2

Reaction notes

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