Triphenylphosphine → HCID 86663729, compound

HRID 579548Notes

Reaction equation

HRID 579548 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:34])[C:9]([CH2:21][CH2:22][CH2:23][CH2:24][B:25]1[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]1)([CH2:17][CH2:18][CH:19]=C)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:35]=[O+][O-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[C:1]([O:5][C:6]([N:8]([CH3:34])[C:9]([CH2:17][CH2:18][CH:19]=[O:35])([CH2:21][CH2:22][CH2:23][CH2:24][B:25]1[O:26][C:27]([CH3:32])([CH3:33])[C:28]([CH3:30])([CH3:31])[O:29]1)[C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24823Ozone2×HCID 66833735HCID 66833735, compound

Product 1

HCID 86663729HCID 86663729, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 2-(tert-butoxycarbonyl(methyl)amino)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butyl)hex-5-enoate (1.10 g, 2.29 mmol) in dichloromethane (30 mL) was cooled to −78° C. and treated with ozone until a pale blue-gray color appeared. After TLC indicated the absence of starting material, the ozone inlet tube was replaced with nitrogen and nitrogen was bubbled through the solution for 20 min to remove any excess ozone. Triphenylphosphine (1.50 g, 5.72 mmol, 2.5 equiv) was added in one portion, the cooling bath was removed and the mixture was stirred for 4 h. The solution was concentrated and purified by MPLC (0-40% ethyl acetate in heptane) gave tert-butyl 2-(tert-butoxycarbonyl(methyl)amino)-2-(3-oxopropyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate as a colorless oil (780 mg, 70%). Rf 0.40 (30% ethyl acetate in heptane). ESI MS found for C25H46BNO7 m/z [484.3 (M+1)].

Workup

  1. customwas bubbled through the solution for 20 min
  2. customto remove any excess ozone
  3. customthe cooling bath was removed
  4. concentrationThe solution was concentrated
  5. custompurified by MPLC (0-40% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-b196ebd750754dddb5239e735de574b3
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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