Sodium Hydroxide → tert-butyl N-(2-methyl-1-oxopropan-2-yl)carbamate

HRID 1707557Notes

Reaction equation

HRID 1707557 reaction equation
[C:1]([NH:8][C:9]([CH3:13])([CH3:12])[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>C(Cl)Cl.C(OCC)C>[C:1]([NH:8][C:9]([CH3:13])([CH3:12])[CH:10]=[O:11])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 14578673tert-butyl N-(1-hydroxy-2-methylpropan-2-yl)carbamate

Product 1

HCID 14578674tert-butyl N-(2-methyl-1-oxopropan-2-yl)carbamateYield 87.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

The resulting N-BOC-2-amino-2-methyl-1-propanol (3.69 g, 19.5 mmol) was dissolved in methylene chloride (74 ml) and added to a stirred suspension of Dess-Martin periodinane (10.75 g, 25.35 mmol; Aldrich Chemical Company, Milwaukee, WI) in methylene chloride (89 ml). After stirring for 20 minutes under nitrogen, the reaction mixture was diluted with diethyl ether (370 ml), poured into sodium hydroxide (148 ml, 1.3M) and stirred for ten minutes. The aqueous sodium hydroxide layer was separated and discarded. The remaining organic solution was washed successively with sodium hydroxide (148 ml, 1.3M) and H2O (185 ml). After drying over magnesium sulfate, the solvent was removed in vacuo to yield 3.21 grams of N-BOC-2-amino-2-methyl-l-propanal.

Workup

  1. stirringstirred for ten minutes
  2. customThe aqueous sodium hydroxide layer was separated
  3. washThe remaining organic solution was washed successively with sodium hydroxide (148 ml, 1.3M) and H2O (185 ml)
  4. dry with materialAfter drying over magnesium sulfate
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-fced2c0de3364ca4baa2d51f0e547a14
Source dataset
uspto-grants-1994_10
Patent number
US05354693

Reaction notes

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