Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → Methyl N-Boc-8-amino-2E-octenoate

HRID 1534834Notes

Reaction equation

HRID 1534834 reaction equation
C1(P(=[CH:20][C:21]([O:23][CH3:24])=[O:22])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:25]([NH:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH:38]=O)([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26]>C(Cl)Cl>[C:25]([NH:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]/[CH:38]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 10536636tert-Butyl 6-oxohexylcarbamate

Product 1

HCID 15679327Methyl N-Boc-8-amino-2E-octenoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 35.28 g (105.5 mmole) methyl (triphenylphosphoranylidene)acetate in 70 mL methylene chloride was added to a solution of 11.36 g (52.76 mmoles) of (7) in 20 mL methylene chloride. After 2 h at room temperature, the solution was concentrated in vacuo to remove most of the solvent and the residue was diluted with ether. The solid was removed by filtration and the filtrate was concentrated and the residue chromatographed (Flash, hexane-ethyl acetate 7:3). The product fraction amounted to 10.7 g of a colorless oil (8).

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. customto remove most of the solvent
  3. additionthe residue was diluted with ether
  4. customThe solid was removed by filtration
  5. concentrationthe filtrate was concentrated
  6. customthe residue chromatographed (Flash, hexane-ethyl acetate 7:3)

Sources & evidence

ORD record
ord-9a65e3f46eb04b82b0d24b496391570b
Source dataset
uspto-grants-1992_02
Patent number
US05091396

Reaction notes

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