Hydroxylamine → Benzyl hydroxycarbamate

HRID 1592347Notes

Reaction equation

HRID 1592347 reaction equation
[NH2:1][OH:2].C([O-])([O-])=O.[K+].[K+].Cl[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]>C(Cl)Cl>[C:10]([NH:1][OH:2])([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 10387Benzyl chloroformateHCID 11430Potassium Carbonate

Product 1

HCID 18907Benzyl hydroxycarbamateYield 135.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of crude amino alcohol 29 (223 g, 1.19 mol) in 1 L of CH2Cl2 was treated with a 1 L aqueous solution of K2CO3 (200 g, 1.45 mol) and cooled in a ice bath. The mixture is stirred vigorously while benzyl chloroformate (225 g, 1.3 mol) is added slowly. After the addition is complete the mixture is stirred an additional 30 min. The organic layer is separated and washed with water, brine and concentrated to give 390 g of crude solid. This is recrystallized from hexane to give 270 g of N-CBZ amino alcohol 30.

Workup

  1. temperaturecooled in a ice bath
  2. additionis added slowly
  3. additionAfter the addition
  4. customThe organic layer is separated
  5. washwashed with water, brine
  6. concentrationconcentrated
  7. customto give 390 g of crude solid
  8. customThis is recrystallized from hexane

Sources & evidence

ORD record
ord-5c2d36e6e2214345b4a7a7991c863404
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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