Cyclopropanemethanol → HCID 68602119, compound

HRID 1185550Notes

Reaction equation

HRID 1185550 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[CH:13]1([CH2:16][OH:17])[CH2:15][CH2:14]1.CCN(C(C)C)C(C)C.[C:27]([O:31][C:32]([N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28]>ClCCl>[CH:13]1([CH2:16][O:17][C:2]([N:37]2[CH2:38][CH2:39][N:34]([C:32]([O:31][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:33])[CH2:35][CH2:36]2)=[O:4])[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 75644CyclopropanemethanolHCID 81531Diisopropylethylamine2×HCID 94429TriphosgeneHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 68602119HCID 68602119, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.3 g triphosgene and 2 g Cyclopropyl-methanol in 40 ml dichloromethane were added 9.1 ml DIPEA dropwise at 0° C. After 1 h, 5.1 g Piperazine-1-carboxylic acid tert-butyl ester and 4.5 ml DIPEA in 7 ml were added at 0° C. The reaction mixture was allowed to warm to RT and stirred for 16 h. Excess triphosgene was destroyed by adding a solution of 2 g NaOH in 120 ml water and stirring for 2 h. The layers were separated and the aqueous layer was extracted with DCM. The combined organic layers were washed with 1M aqueous hydrochloric acid, dried over MgSO4 and concentrated. The crude product thus obtained was purified was used in the next reaction step. Yield: 7.9 g.

Workup

  1. customExcess triphosgene was destroyed
  2. additionby adding a solution of 2 g NaOH in 120 ml water
  3. stirringstirring for 2 h
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with DCM
  6. washThe combined organic layers were washed with 1M aqueous hydrochloric acid
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0a2f0ad318ac43baba81e1c6fd5a5744
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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