HCID 18391514, compound → HCID 18391512, compound

HRID 1586109Notes

Reaction equation

HRID 1586109 reaction equation
[C:1]([N:11]1[CH2:18][C@@H:17]([O:19]C(=O)C)[CH2:16][C@@H:12]1[C:13]([OH:15])=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH3:23][CH2:24][O-].[Na+].CCO>C(O)C>[CH2:23]([O:15][C:13](=[O:14])[C@H:12]1[CH2:16][C@H:17]([OH:19])[CH2:18][N:11]1[C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])[CH3:24]

Participants

4

Reactant 2

HCID 18391514HCID 18391514, compoundHCID 23706232Ethanol sodium ethoxide

Product 1

HCID 18391512HCID 18391512, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirring solution of N-CBZ-trans-4-acetoxy-D-proline (2.45 g, 7.31 mmol) in ethanol (50 mL) was added freshly prepared NaOEt/EtOH (0.017 g, 0.7 mmol of Na dissolved in 1 mL of EtOH). After stirring at room temperature for 20 minutes, the reaction was quenched with NH4Cl (0.1 g), and concentrated in vacuo to an oily solid. The desired alcohol was isolated (2.01 g, 94%) as a colorless oil by diluting the residue with ethyl ether (50 mL), filtering the solution through Celite, washing the filter cake with ethyl ether, and concentrating the combined filtrate and washings in vacuo. The alcohol was sufficiently pure to use directly in the next step: [α]25D +59° (c, 1.04 CHCl3); Spectra were identical in all respects to those of the enantiomer N-(benzyloxycarbonyl)-trans-4-hydroxy-L-proline ethyl ester; LRMS (CI, 70 eV, isobutane) m/e 294 (MH+, 100), 250 (98), 220 (24), 158 (25), 91 (89); HRMS (EI, 50 eV) m/e 293.1272 (293.1263 calcd for C15H19NO5).

Workup

  1. customthe reaction was quenched with NH4Cl (0.1 g)
  2. concentrationconcentrated in vacuo to an oily solid

Sources & evidence

ORD record
ord-12b319033cdd4cddb41194fb64088788
Source dataset
uspto-grants-1999_08
Patent number
US05942537

Reaction notes

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