Cesium carbonate → HCID 59300472, compound

HRID 603452Notes

Reaction equation

HRID 603452 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C@H:7]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:6][CH2:5]2.[C:17]([O-:20])([O-])=[O:18].[Cs+].[Cs+].[NH4+:23].[Cl-]>CN(C=O)C>[C:4]([O:20][C:17]([NH:23][CH2:6][CH2:7][CH2:11][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C@H:7]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:6][CH2:5]2)=[O:18])([CH3:8])([CH3:5])[CH3:3]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 16110404ethyl 2-[(1S)-5-hydroxy-2,3-dihydro-1H-inden-1-yl]acetate

Product 1

HCID 59300472HCID 59300472, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl [(1S)-5-hydroxy-2,3-dihydro-1H-inden-1-yl]acetate (Example 6, 1 g, 4.54 mmol) and (3-Boc-amino)propyl bromide (1.51 g, 6.36 mmol) in DMF (40 mL) was added Cs2CO3 (2.96 g, 9.08 mmol). The mixture was stirred at rt for 18 h, and diluted with a saturated solution of NH4Cl. The mixture was extracted with Et2O and the combined ether extracts were dried (MgSO4), filtered, and concentrated under reduced pressure. The product (2.15 g, 94%) was isolated by silica gel column chromatography (2:1 hexanes/EtOAc). 1H NMR (400 MHz, CD2Cl2) δ 7.05 (d, 1H), 6.77 (s, 1H), 6.69 (dd, 1H), 4.16 (q, 2H), 3.99 (t, 2H), 3.48 (qt, 1H), 3.34-3.25 (m, 2H), 2.95-2.78 (m, 2H), 2.71 (dd, 1H), 2.45-2.33 (m, 2H), 1.95 (qt, 2H), 1.80-1.72 (m, 1H), 1.44 (s, 9H), 1.28 (t, 3H).

Workup

  1. extractionThe mixture was extracted with Et2O
  2. dry with materialthe combined ether extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-96ca0e5ca2474d149c2dad43bbfdbb3c
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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