Citric Acid → tert-butyl N-(2-amino-2-methylpropyl)carbamate

HRID 1393642Notes

Reaction equation

HRID 1393642 reaction equation
[CH3:1][C:2]([NH2:6])([CH3:5])[CH2:3][NH2:4].[CH3:7][C:8]([O:11][C:12](ON=C(C1C=CC=CC=1)C#N)=[O:13])([CH3:10])[CH3:9].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl.C(Cl)(Cl)Cl>[NH2:6][C:2]([CH3:5])([CH3:1])[CH2:3][NH:4][C:12](=[O:13])[O:11][C:8]([CH3:10])([CH3:9])[CH3:7]

Participants

6

Reactant 3

HCID 311Citric AcidHCID 131282-MethylpropylenediamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

Product 1

HCID 17909918tert-butyl N-(2-amino-2-methylpropyl)carbamateYield 74%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

2-Methylpropane-1,2-diamine (5.0 g) was dissolved in dichloromethane (200 ml) and stirred for 15 minutes at 0° C. A solution of BOC-ON (15 g) in dichloromethane (60 ml) was added dropwise thereto and then stirred for 2 hours at room temperature. The reaction mixture was diluted with chloroform with ice cooling and then acidified by 10% citric acid solution, and the organic phase was separated. The aqueous phase was alkalinized by 5 N sodium hydroxide solution, then extracted with ethyl acetate, and the extract was dried over sodium sulfate anhydrous. The product was concentrated under reduced pressure to give t-butyl (2-amino-2-methyl-1-propyl)carbamate (7.9 g, Y.:74%).

Workup

  1. stirringstirred for 2 hours at room temperature
  2. customthe organic phase was separated
  3. extractionextracted with ethyl acetate
  4. dry with materialthe extract was dried over sodium sulfate anhydrous
  5. concentrationThe product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8013d801bb364a62b709c54cd79f8774
Source dataset
uspto-grants-2008_03
Patent number
US07345180B2

Reaction notes

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