Triethylamine → HCID 15117273, compound

HRID 1029651Notes

Reaction equation

HRID 1029651 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([C:13](O)=[O:14])[CH2:9][CH2:8]1)=[O:6])[CH:2]=[CH2:3].C(N(CC)CC)C.ClC(OCC(C)C)=O>O1CCCC1>[CH2:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH2:13][OH:14])[CH2:9][CH2:8]1)=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 14252917HCID 14252917, compound

Product 1

HCID 15117273HCID 15117273, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-allyloxycarbonyl-4-carboxypiperidine (37 g) in tetrahydrofuran (400 ml) were added triethylamine (31 ml) and isobutyl chloroformate (27 ml) at -30° C. After stirring for 30 minutes at 0° C., the precipitate was filtered off. The obtained solution was added dropwise to the solution of sodium borohydride (13 g) in water (100 ml) at 0° C. After stirring for 1 hour at 0° C., sodium chloride was added to saturate the aqueous layer, and the organic layer was separated. The dried organic layer was evaporated and then the residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (1:1-1:2, V/V) to give 1-allyloxycarbonyl-4-hydroxymethylpiperidine (24 g).

Workup

  1. filtrationthe precipitate was filtered off
  2. additionThe obtained solution was added dropwise to the solution of sodium borohydride (13 g) in water (100 ml) at 0° C
  3. stirringAfter stirring for 1 hour at 0° C.
  4. additionsodium chloride was added
  5. concentrationto saturate the aqueous layer
  6. customthe organic layer was separated
  7. customThe dried organic layer was evaporated
  8. customthe residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (1:1-1:2, V/V)

Sources & evidence

ORD record
ord-2786ab55a50a40beab53b2915e9d53e8
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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