HCID 86596939, compound → HCID 69286679, compound

HRID 2225232Notes

Reaction equation

HRID 2225232 reaction equation
[CH:1]([C@H:5]1[C@@H:14]([NH:15]C(=O)[O-])[CH2:13][CH2:12][C:7]2([O:11][CH2:10][CH2:9][O:8]2)[CH2:6]1)=[CH:2][CH2:3][CH3:4]>CO.[Pd]>[CH2:1]([C@H:5]1[C@@H:14]([NH2:15])[CH2:13][CH2:12][C:7]2([O:8][CH2:9][CH2:10][O:11]2)[CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 86596939HCID 86596939, compound

Product 1

HCID 69286679HCID 69286679, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of ((7S,8S)-7-(but-1-enyl)-1,4-dioxa-spiro[4.5]dec-8-yl)-carbamate (7.7 g, 0.0221 mol) in 80 mL of MeOH was treated with 1.5 g of 10% Pd/C and hydrogenated overnight at 55 psi. The mixture was filtered through Celite and concentrated on a rotary evaporator to give 4.3 g of (7R,8S)-7-(butyl)-8-(amino)-1,4-dioxa-spiro[4.5]decane. This was used without further purification.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-f312d14a2b0742d1bac9c726cf285744
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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