Diisopropyl Ether → HCID 86626445, compound

HRID 661479Notes

Reaction equation

HRID 661479 reaction equation
[CH:1]1([NH:4][CH2:5][C@@H:6]2[C@@H:10]([OH:11])[CH2:9][N:8]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[CH2:7]2)[CH2:3][CH2:2]1.CO.[ClH:24].C(OC(C)C)(C)C>C(OCC)(=O)C>[ClH:24].[CH:1]1([NH:4][CH2:5][C@@H:6]2[C@@H:10]([OH:11])[CH2:9][N:8]([C:12]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:13])[CH2:7]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 21893726Hydrochloride methanolHCID 54751762HCID 54751762, compound

Product 1

HCID 86626445HCID 86626445, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4.86 L of ethyl acetate was added to 345 g of benzyl (3S,4R)-3-cyclopropylaminomethyl-4-hydroxypyrrolidine-1-carboxylate (1.20 mol) to dissolve the compound. While this solution was stirred, 1.04 L of a 10% hydrogen chloride methanol solution was added at an internal temperature of 21° C. Following the formation of crystals (internal temperature of 20° C.), the mixture was kept stirred for 15 minutes. Subsequently, 9.72 L of diisopropyl ether was added slowly and the mixture was further stirred for 30 minutes. The resulting crystals were collected by filtration, washed with 0.52 L of ethyl acetate, and drained for 30 minutes. The product was then dried by air-blowing at 60° C. for 4 hours to give 350 g of the title compound as white powder crystals (90% yield in the 2 steps).

Workup

  1. dissolutionto dissolve the compound
  2. customthe formation of crystals (internal temperature of 20° C.)
  3. stirringthe mixture was kept stirred for 15 minutes
  4. stirringthe mixture was further stirred for 30 minutes
  5. filtrationThe resulting crystals were collected by filtration
  6. washwashed with 0.52 L of ethyl acetate
  7. customThe product was then dried by air-blowing at 60° C. for 4 hours

Sources & evidence

ORD record
ord-0e06d0677910409db88112863163bbcf
Source dataset
uspto-grants-2011_12
Patent number
US08084622B2

Reaction notes

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