Tetrapropylammonium → HCID 86622958, compound

HRID 1715413Notes

Reaction equation

HRID 1715413 reaction equation
C[N+]1([O-])CCOCC1.[C:9]([O:13][C:14](=[O:28])[N:15]([CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH2:26][OH:27])[CH:20]=1)[CH3:16])([CH3:12])([CH3:11])[CH3:10].C([N+](CCC)(CCC)CCC)CC>C(Cl)Cl>[C:9]([O:13][C:14](=[O:28])[N:15]([CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH:26]=[O:27])[CH:20]=1)[CH3:16])([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 9559TetrapropylammoniumHCID 82029Methyl morpholine oxideHCID 68505467HCID 68505467, compound

Product 1

HCID 86622958HCID 86622958, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

NMO (607 mg, 4.35 mmol) was added to a sol. of [2-(4-chloro-3-hydroxymethyl-phenyl)-ethyl]-methyl-carbamic acid tert-butyl ester (435 mg, 1.45 mmol) in CH2Cl2 (30 mL). The mixture was stirred for 30 min, and tetrapropylammonium perrhutenate (51.0 mg, 0.145 mmol) was added. The mixture was stirred for 1 h, and was filtered over Celite. The filtrate was evaporated under reduced pressure. Purification of the crude by FC (CH2Cl2/MeOH 19:1) yielded the title compound (330 mg, 76%). LC-MS: tR=1.00 min.

Workup

  1. stirringThe mixture was stirred for 1 h
  2. filtrationwas filtered over Celite
  3. customThe filtrate was evaporated under reduced pressure
  4. customPurification of the crude by FC (CH2Cl2/MeOH 19:1)

Sources & evidence

ORD record
ord-bfbce9977c5c4f129459a0975cb85632
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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