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Diisopropylethylamine → n-Trimethylsilylethoxycarbonyl-1,2-diaminoethanehydrochloride

HRID 355494
Notes
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Reaction equation

HRID 355494 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH2:11])=[O:7])(C)(C)[CH3:2].C(N(C(C)C)CC)(C)C.[CH3:21][Si:22](CCOC([Cl:30])=O)([CH3:24])[CH3:23]>C1COCC1.ClCCl>[ClH:30].[CH3:21][Si:22]([CH2:2][CH2:1][O:5][C:6]([NH:8][CH2:9][CH2:10][NH2:11])=[O:7])([CH3:24])[CH3:23]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 187201N-BOC-ethylenediamineHCID 109101682-(Trimethylsilyl)ethyl chloroformate

Product 1

HCID 23511190n-Trimethylsilylethoxycarbonyl-1,2-diaminoethanehydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent
HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
0 °C

Procedure

N-(t-Butyloxycarbonyl)-1,2-diaminoethane (8.0 g, 50 mmol) is dissolved in THF (200 mL), diisopropylethylamine (6.5 g, 50 mmol) is added and the solution cooled to 0° C. To this cold solution is added dropwise trimethylsilylethoxycarbonylchloride (9.0 g, 50 mmol) over 10 minutes. After stirring an additional 30 minutes the reaction is filtered and the filtrate is evaporated to an oil. This oil is dissolved in 100 mL of diethyl ether and washed with dilute HCl solution (3×25 mL), dried, filtered and evaporated to give an oil. The oil is dissolved in 100 mL of dichloromethane and dry HCl gas is bubbled through the solution for 30 minutes and the reaction stirred for 1 hour. The reaction is diluted with 200 mL of cold diethyl ether and allowed to stand at -5° C. for 12 hours. The colorless solid formed is collected and stored protected from moisture.

Workup

  1. filtrationis filtered
  2. customthe filtrate is evaporated to an oil
  3. dissolutionThis oil is dissolved in 100 mL of diethyl ether
  4. washwashed with dilute HCl solution (3×25 mL)
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customto give an oil
  9. customdry HCl gas is bubbled through the solution for 30 minutes
  10. stirringthe reaction stirred for 1 hour
  11. additionThe reaction is diluted with 200 mL of cold diethyl ether
  12. waitto stand at -5° C. for 12 hours
  13. customThe colorless solid formed
  14. customis collected

Sources & evidence

ORD record
ord-71f9fd10854a4b8bb1c63b4acc0d0f21
Source dataset
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05831014

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes