Hydrazine → tert-butyl (3R)-3-(aminooxy)pyrrolidine-1-carboxylate

HRID 710955Notes

Reaction equation

HRID 710955 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 117988618(R)-tert-butyl 3-((1,3-dioxoisoindolin-2-yl)oxy)pyrrolidine-1-carboxylate

Product 1

HCID 86693911tert-butyl (3R)-3-(aminooxy)pyrrolidine-1-carboxylateYield 78.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To (R)-tert-butyl 3-((1,3-dioxoisoindolin-2-yl)oxy)pyrrolidine-1-carboxylate (2.73 g, 8.21 mmol) prepared following a procedure analogous to Reference Example 7 from (R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate in methanol (43 mL) was gradually added hydrazine.monohydrate (1.54 g), followed by stirring for 2 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 1.30 g of the title compound (yield 78.3%).

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-1290a9f1bb63431eb8d8c63e164deadc
Source dataset
uspto-grants-2015_11
Patent number
US09181250B2

Reaction notes

Loading…