Hydrazine hydrate (1:1) → HCID 178418701, compound

HRID 8773Notes

Reaction equation

HRID 8773 reaction equation
[C:1]1([CH2:7][C:8](=O)[CH2:9][C:10]([C:12]2([CH2:25][CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[NH2:37][NH2:38]>C(O)C>[C:21]([O:20][C:18]([N:15]1[CH2:16][CH2:17][C:12]([CH2:25][CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])([C:10]2[NH:38][N:37]=[C:8]([CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:9]=2)[CH2:13][CH2:14]1)=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21983978tert-Butyl 4-(4-phenyl-1,3-dioxobut-1-yl)-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate

Product 1

HCID 178418701HCID 178418701, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of tert-butyl 4-(4-phenyl-1,3-dioxobut-1-yl)-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate (343 mg, 0.68 mmol) from Step G in ethanol (7 mL) was added hydrazine hydrate (0.040 mL, 0.82 mmol). The reaction was heated at 85° C. for 3 h and was then concentrated in vacuo. The residue was purified by flash chromatography (30% ethyl acetate in hexanes) to afford the title product (243 mg).

Workup

  1. concentrationwas then concentrated in vacuo
  2. customThe residue was purified by flash chromatography (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-b1cbf72bde5741aa9e5793f4199bac7c
Source dataset
uspto-grants-2006_08
Patent number
US07091211B2

Reaction notes

Loading…