Ammonia → Tert-butyl 2-carbamoyl-4-hydroxypyrrolidine-1-carboxylate

HRID 622451Notes

Reaction equation

HRID 622451 reaction equation
ClC(OCC)=O.[C:7]([O:11][C:12]([N:14]1[CH2:18][C@H:17]([OH:19])[CH2:16][C@H:15]1[C:20]([OH:22])=O)=[O:13])([CH3:10])([CH3:9])[CH3:8].C([N:25](CC)CC)C.N>O1CCCC1>[C:7]([O:11][C:12]([N:14]1[CH2:18][CH:17]([OH:19])[CH2:16][CH:15]1[C:20](=[O:22])[NH2:25])=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 88804(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Product 1

HCID 14796647Tert-butyl 2-carbamoyl-4-hydroxypyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4.98 ml of ethyl chloroformate in 50 ml of anhydrous tetrahydrofuran was added, under cooling at -+° C., to a solution of 11.0 g of 1-(t-butoxycarbonyl)-(2S,4R)-4-hydroxy-2-pyrrolidinecarboxylic acid and 7.25 ml of triethylamine in 160 ml of anhydrous tetrahydrofuran, and the mixture was stirred at the same temperature for one hour. 50 ml of concentrated aqueous ammonia were then added, at the same temperature, and the mixture was allowed to stand while its temperature rose to ambient. The reaction mixture was stirred for one hour, and then concentrated by evaporation under reduced pressure. A saturated aqueous solution of sodium chloride was added to the concentrate, which was then extracted three times with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure, to give 7.70 g of (2S,4R)-1-(t-butoxycarbonyl-2-carbamoyl-4-hydroxypyrrolidine.

Workup

  1. concentrationconcentrated by evaporation under reduced pressure
  2. additionA saturated aqueous solution of sodium chloride was added to the concentrate, which
  3. extractionwas then extracted three times with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-70cdbaa57500486c9660d53424a32be8
Source dataset
uspto-grants-1988_09
Patent number
US04771046

Reaction notes

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