Sodium sulfate decahydrate → tert-Butyl [4-(hydroxymethyl)benzyl]carbamate

HRID 348706Notes

Reaction equation

HRID 348706 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:12][CH:11]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[C:21]([O:20][C:18](=[O:19])[NH:17][CH2:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][OH:8])=[CH:15][CH:14]=1)([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 14221817Methyl 4-((((1,1-dimethylethoxy)carbonyl)amino)methyl)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 2794813tert-Butyl [4-(hydroxymethyl)benzyl]carbamateYield 85.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (5.21 g) was suspended in THF (243 ml). Then, a solution of the compound (24.3 g) obtained in Example 103-1 in THF (243 ml) was gradually added to the suspension over 50 minutes while stirring under ice-cooling, followed by stirring at room temperature for 1 hour. The reaction solution was added with sodium sulfate decahydrate and a 20% sodium hydroxide aqueous solution and then filtrated through Celite. The filtrate was concentrated under reduced pressure and dried under vacuum, thereby obtaining the subject compound (18.5 g).

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for 1 hour
  3. filtrationa 20% sodium hydroxide aqueous solution and then filtrated through Celite
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customdried under vacuum

Sources & evidence

ORD record
ord-e58cf39c14454272ab1d04d153b8fee3
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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