Toluene → HCID 131730314, compound

HRID 1948308Notes

Reaction equation

HRID 1948308 reaction equation
[OH-].[Na+].[CH2:3](Br)[CH:4]=[CH2:5].[C:7]([O:11][C:12]([NH:14][C@H:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][C@H:16]1[OH:26])=[O:13])([CH3:10])([CH3:9])[CH3:8].C1(C)C=CC=CC=1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.CCOC(C)=O.O>[CH2:24]([O:23][C:21]([N:18]1[CH2:19][CH2:20][C@H:15]([NH:14][C:12]([O:11][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:13])[C@H:16]([O:26][CH2:5][CH:4]=[CH2:3])[CH2:17]1)=[O:22])[CH3:25]

Participants

8

Reactant 4

HCID 1140TolueneHCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 131730315HCID 131730315, compound

Product 1

HCID 131730314HCID 131730314, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 50% aqueous solution of sodium hydroxide (3 ml) was added to a suspension of allyl bromide (693 mg, 5.70 mmol), cis(±)ethyl 4-[(tert-butoxycarbonyl)amino]-3-hydroxypiperidine-1-carboxylate (reference: C. H. Lee et al. Syn. Commun., 2001, 31, 1081), (750 mg, 2.6 mmol), benzyltriethylammonium chloride (4 mg, cat.) and toluene (8 ml). The resultant mixture was stirred overnight at room temperature. The reaction mixture was diluted with EtOAc (150 ml) and water (35 ml). The organic phase was separated and the aqueous phase was back extracted with EtOAc (2×30 ml). The combined organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated. The crude residue was purified by flash column chromatography (hexane/EtOAc, 3:2) to yield 734 mg of the title compound. MS (ES)(M+H): 329. for C16H28N2O5; NMR: 1.28 (t, 3H), 1.47 (s, 9H), 1.68 (m, 2H), 2.88 (brt, 2H), 3.50 (m, 1H), 3.68 (m, 1H), 3.90 (m, 1H), 4.00-4.45 (m, 3H), 4.10 (q, 2H), 4.92 (brs, 1H), 5.20 (m, 2H), 5.86 (m, 1H).

Workup

  1. customThe organic phase was separated
  2. extractionthe aqueous phase was back extracted with EtOAc (2×30 ml)
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by flash column chromatography (hexane/EtOAc, 3:2)

Sources & evidence

ORD record
ord-46e4a571585b4f57a26a34bf6f5c5eec
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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