Lithium diisopropylamide → HCID 86760318, compound

HRID 857768Notes

Reaction equation

HRID 857768 reaction equation
[CH2:1]([O:8][C:9](=[O:24])[CH2:10][N:11]([CH2:20][CH2:21][CH:22]=[CH2:23])[C@@H:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].CC([N-]C(C)C)C>[Br-].[Zn+2].[Br-]>[CH3:23][C@H:22]1[CH2:21][CH2:20][N:11]([CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[C@H:10]1[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:24]

Participants

4

Reactant 2

HCID 2724682Lithium diisopropylamideHCID 69655804HCID 69655804, compound

Product 1

HCID 86760318HCID 86760318, compound

Reagents, catalysts & solvents 1

HCID 10421208Zinc bromideCatalyst

Conditions

Temperature
0 °C

Procedure

The title compound was prepared from (R)-[but-3-enyl-(1-phenyl-ethyl)-amino]-acetic acid benzyl ester essentially according to the cyclization protocol described in Karoyan, P.; Chassaing, G. Tetrahedron: Asymm. 1997, 8, 2025–2032 with the following modifications: LDA was added at −40° C., then the solution was warmed to 0° C. for 10 min, then re-cooled to −40° C. for the zinc bromide addition. The transmetallation step was omitted and the anion was quenched directly with 2:1 saturated NH4Cl:ammonium hydroxide. Extractive workup (Et2O) afforded an orange oil which was purified by silica gel chromatography (5–10% EtOAc-hexanes) to give the title compound as a yellow oil.

Workup

  1. customthe anion was quenched directly with 2:1 saturated NH4Cl
  2. customExtractive workup (Et2O) afforded an orange oil which
  3. customwas purified by silica gel chromatography (5–10% EtOAc-hexanes)

Sources & evidence

ORD record
ord-ef415a0345f94d03bf5d4a94315cd1a3
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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