4-Bromophenol → HCID 66740851, compound

HRID 715912Notes

Reaction equation

HRID 715912 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.O[CH2:10][C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][C@@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 78084-BromophenolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 643448(S)-(-)-N-Boc-prolinol

Product 1

HCID 66740851HCID 66740851, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-bromophenol (1.73 g) and tert-butyl (2S)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (4.0 g) in tetrahydrofuran (50 ml),triphenylphosphine (3.1 g) and a solution of diisopropyl azodicarboxylate (2.4 g) in tetrahydrofuran (10 ml) were added, and the mixture was heated to reflux for 2 hours. After cooling, the reaction solution was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain the title compound (3.5 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperatureAfter cooling
  4. concentrationthe reaction solution was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-df37563c37e24b298b45e881957cb05c
Source dataset
uspto-grants-2015_11
Patent number
US09187489B2

Reaction notes

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