HCID 66674018, compound → HCID 66675025, compound

HRID 421936Notes

Reaction equation

HRID 421936 reaction equation
[C:1]([CH2:3][CH:4]1[CH2:11][N:10]2[C:12]3[CH:13]=[C:14]([C:25]([O:27][CH3:28])=[O:26])[CH:15]=[CH:16][C:17]=3[C:18]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[C:9]2[C:8]2[CH:29]=[CH:30][CH:31]=[CH:32][C:7]=2[O:6][CH2:5]1)#[N:2]>CO.[Pt](=O)=O>[NH2:2][CH2:1][CH2:3][CH:4]1[CH2:11][N:10]2[C:12]3[CH:13]=[C:14]([C:25]([O:27][CH3:28])=[O:26])[CH:15]=[CH:16][C:17]=3[C:18]([CH:19]3[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]3)=[C:9]2[C:8]2[CH:29]=[CH:30][CH:31]=[CH:32][C:7]=2[O:6][CH2:5]1

Participants

4

Reactant 1

HCID 66674018HCID 66674018, compound

Product 1

HCID 66675025HCID 66675025, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

Platinum(IV) oxide (0.5 eq.) was added to a solution of methyl 7(R,S)-(cyanomethyl)-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (0.20 M) in MeOH. The atmosphere in the reaction vessel was exchanged for H2, and the reaction stirred vigorously at RT for 4 h. The reaction vessel was flushed with N2, and the reaction mixture filtered through a plug of CELITE (washing well with MeOH and EtOAc). Volatiles were removed in vacuo to afford the crude product which was purified by FC (EtOAc/MeOH/Et3N 93:5:2) affording the product as a yellow oil (12%). (ES+) m/z 433 (M+H)+.

Workup

  1. customThe reaction vessel was flushed with N2
  2. filtrationthe reaction mixture filtered through a plug of CELITE (
  3. washwashing well with MeOH and EtOAc)
  4. customVolatiles were removed in vacuo
  5. customto afford the crude product which
  6. customwas purified by FC (EtOAc/MeOH/Et3N 93:5:2)

Sources & evidence

ORD record
ord-21e355323244424083b0e8f0e89b6254
Source dataset
uspto-grants-2012_01
Patent number
US08101595B2

Reaction notes

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