Di-tert-butyl 2-[[[2-(benzylcarboxy)propyl]tert-butoxyphosphinyl]methyl]pentanedioate → Di-tert-butyl 2-[[[2-(carboxy)propyl]tert-butoxy-phosphinyl]methyl]pentanedioate

HRID 842594Notes

Reaction equation

HRID 842594 reaction equation
C([O:8][C:9]([CH:11]([CH3:38])[CH2:12][P:13]([CH2:20][CH:21]([CH2:29][CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:10])C1C=CC=CC=1>[Pd].C(OCC)(=O)C>[C:9]([CH:11]([CH3:38])[CH2:12][P:13]([CH2:20][CH:21]([CH2:29][CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14])([OH:10])=[O:8]

Participants

4

Reactant 1

HCID 18418074Di-tert-butyl 2-[[[2-(benzylcarboxy)propyl]tert-butoxyphosphinyl]methyl]pentanedioate

Product 1

HCID 18418070Di-tert-butyl 2-[[[2-(carboxy)propyl]tert-butoxy-phosphinyl]methyl]pentanedioateYield 100.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of di-tert-butyl 2-[[[2-(benzylcarboxy)propyl]tert-butoxyphosphinyl]methyl]pentane1,5-dioate (8.9 g, 16.1 mmol), palladium on carbon catalyst (10%, 1.0 g) and ethyl acetate (100 ml) was shaken under hydrogen (60 psi) for 16 hours. The reaction mixture was filtered over celite and the filtrate was concentrated under reduced pressure leaving a clear oil (7.5 g, 100%). 1H NMR (CDCl3): δ1.3 (d, 3H), 1.4-1.5 (m, 27H), 1.8 (m, 2H), 1.9 (m, 2H), 2.2 (m, 4H), 2.7 (m, 1H), 2.9 (m, 1H).

Workup

  1. filtrationThe reaction mixture was filtered over celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fa0a17eb36324efbaee3fbdcaac34085
Source dataset
uspto-grants-2002_04
Patent number
US06376478B1

Reaction notes

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