Ethyl Acetate → methyl 14-cyclohexyl-7-formyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-1-carboxylate

HRID 1669482Notes

Reaction equation

HRID 1669482 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11](C(OC)=O)=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2C=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17][CH:16]([CH2:26][OH:27])[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[CH2:33][O:34][C:35]([CH3:37])=[O:36]>C(Cl)Cl>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2=[C:37]([C:35]([O:34][CH3:33])=[O:36])[CH:23]=[CH:24][CH:25]=[C:19]2[O:18][CH2:17][CH:16]([CH:26]=[O:27])[CH2:15]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 66674539HCID 66674539, compound

Product 1

HCID 86627908methyl 14-cyclohexyl-7-formyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-1-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution (0.03 M) of methyl 14-cyclohexyl-7-(hydroxymethyl)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (prepared as described in example 13, steps 1-2) in DCM was added to a solution of DMP (0.04 M; 1.25 eq) in DCM at RT. The reaction was then left to stir at RT for 1 h. The mixture was diluted with EtOAc and washed with a 1:1 mixture of sat. aq. NaHCO3 and sodium thiosulfate (aq) (3×) before washing with brine, drying (Na2SO4), filtering and concentrating in vacuo to afford the product as a tinted glass (98%). The material was taken on without further purification. (ES+) m/z 418 (M+H)+; 436 (M+H2O+H)+.

Workup

  1. waitThe reaction was then left
  2. washwashed with a 1:1 mixture of sat. aq. NaHCO3 and sodium thiosulfate (aq) (3×)
  3. washbefore washing with brine
  4. dry with materialdrying (Na2SO4)
  5. filtrationfiltering
  6. concentrationconcentrating in vacuo

Sources & evidence

ORD record
ord-21205700a83942249497e73f5dd34d08
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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