Hydrazine → HCID 21912759, compound

HRID 1245603Notes

Reaction equation

HRID 1245603 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([C:20](=O)[CH3:21])[C:15](OCC)=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:23][NH2:24]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:15](=[O:16])[NH:23][NH:24][C:20]=2[CH3:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 9321HydrazineHCID 21912790HCID 21912790, compound

Product 1

HCID 21912759HCID 21912759, compound

Procedure

A solution of 595 mg (1.9 mmol) of ethyl 2-(R/S)-(1-tert-butoxycarbonyl-piperidin-4-yl)-3-oxo-butanoate (from Step B) and 0.06 mL (1.9 mmol) of hydrazine in 10 mL of xylenes was heated at reflux for 2 h. The resulting mixture was cooled to rt and the solid that precipitated was filtered and dried to afford the title compound. 1H-NMR (500 MHz, CD3OD) δ 1.45 (s, 9H), 1.60 (app d, J=12.0, 2H), 1.83 (dq, J=4.0, 13.0, 2H), 2.14 (s, 3H), 2.52–2.58 (m, 1H), 2.65–2.85 (br s, 2H), 4.13 (d, J=13.5, 2H), 4.81 (s, 2H).

Workup

  1. temperatureat reflux for 2 h
  2. customthe solid that precipitated
  3. filtrationwas filtered
  4. customdried

Sources & evidence

ORD record
ord-887dbd133e044a23bcef184a54f9aadb
Source dataset
uspto-grants-2006_10
Patent number
US07125887B2

Reaction notes

Loading…