Hydrazine → tert-Butyl (S)-3-(aminooxy)pyrrolidine-1-carboxylate

HRID 710956Notes

Reaction equation

HRID 710956 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[O:12][C@H:13]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]1.O[C@@H]1CCN(C(OC(C)(C)C)=O)C1.NN>CO>[NH2:3][O:12][C@H:13]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]1

Participants

5

Reactant 3

HCID 9321HydrazineHCID 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylateHCID 59704735(S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59596622tert-Butyl (S)-3-(aminooxy)pyrrolidine-1-carboxylateYield 98.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-tert-Butyl 3-((1,3-dioxoisoindolin-2-yl)oxy)pyrrolidine-1-carboxylate (2.91 g, 8.77 mmol) prepared from (R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate following a procedure analogous to Reference Example 7 was gradually added to methanol (43 mL) and hydrazine.monohydrate (1.54 g), followed by stirring for 3 hours. The reaction solution was filtered and the residue resulting from distilling off the filtrate under reduced pressure was subjected to silica gel column chromatography (hexane/ethyl acetate=4/1→0/1) to afford 1.75 g of the title compound (yield 98.7%).

Workup

  1. filtrationThe reaction solution was filtered
  2. customthe residue resulting
  3. distillationfrom distilling off the filtrate under reduced pressure

Sources & evidence

ORD record
ord-c7e6955c148846fcb09754ef86cf7533
Source dataset
uspto-grants-2015_11
Patent number
US09181250B2

Reaction notes

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