1-Butanol → 561314-42-9

HRID 749278Notes

Reaction equation

HRID 749278 reaction equation
O.[NH2:2][NH2:3].[C:4]([N:11]1[CH2:16][CH2:15][CH:14]([C:17](OC)=O)[CH2:13][C:12]1=C)([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[CH2:22]([OH:26])CCC>>[C:7]([O:6][C:4]([N:11]1[CH2:12][CH2:13][C:14]2([NH:3][NH:2][C:22](=[O:26])[CH2:17]2)[CH2:15][CH2:16]1)=[O:5])([CH3:8])([CH3:9])[CH3:10]

Participants

4

Reactant 3

HCID 2631-Butanol2×HCID 24654Hydrazine hydrate (1:1)HCID 67527918N-BOC-4-methoxycarbonyl-methylenepiperidine

Product 1

HCID 57426043561314-42-9Yield 63%

Conditions

Temperature
120 °C

Procedure

A solution of hydrazine monohydrate (5.28 mL, 108.8 mmol) in n-butanol (20 mL) was added dropwise to a solution of N-BOC-4-methoxycarbonyl-methylenepiperidine (1.39 g, 5.44 mmol) in n-butanol (120 mL) at rt. The mixture was stirred for 15 h at 120° C. and the mixture allowed to cool to rt. The solvent was removed by evaporation under reduced pressure, the residue partitioned between ethyl acetate and water and the organic layer dried over sodium sulphate, filtered and evaporated to dryness. Purification of the residue by silica gel column chromatography, eluting with a stepwise gradient of 3-6% methanol in dichloromethane, afforded the desired compound (0.88 g, 63 %) as white solid.

Workup

  1. temperatureto cool to rt
  2. customThe solvent was removed by evaporation under reduced pressure
  3. customthe residue partitioned between ethyl acetate and water
  4. dry with materialthe organic layer dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customPurification of the residue by silica gel column chromatography
  8. washeluting with a stepwise gradient of 3-6% methanol in dichloromethane

Sources & evidence

ORD record
ord-c77334c2ea434cfda2c7e18b9f787a1f
Source dataset
uspto-grants-2008_07
Patent number
US07402590B2

Reaction notes

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