Methyl morpholine oxide → tert-Butyl 6-oxohexylcarbamate

HRID 1007288Notes

Reaction equation

HRID 1007288 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 4146612tert-Butyl N-(6-hydroxyhexyl)carbamate

Product 1

HCID 10536636tert-Butyl 6-oxohexylcarbamateYield 66.6%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.0 g of 6-tert-butoxycarbonylamino-1-hexanol in 20 mL of methylene chloride was combined with 3 g of a 4 angstrom molecular sieve, 808 mg of N-methylmorpholine-N-oxide and a catalytic amount of tetrapropylammonium perruthenate, and stirred for 24 hours. The reaction solution was filtered through Celite, and concentrated. The residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1) to obtain 660 mg of the desirable compound.

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-c5c189e8642b4832b90f82f83c6aaf11
Source dataset
uspto-grants-2004_09
Patent number
US06794389B2

Reaction notes

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