HCID 68576452, compound → HCID 68576999, compound

HRID 639513Notes

Reaction equation

HRID 639513 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@H:8]3[N:19]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:17][C@@:14]4([C:15]=2[CH:16]=1)[C@H:9]3[CH2:10][CH2:11][CH2:12][CH2:13]4)=[CH2:2].[H][H]>CO.[Pd]>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@H:8]3[N:19]([C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:18][CH2:17][C@@:14]4([C:15]=2[CH:16]=1)[C@H:9]3[CH2:10][CH2:11][CH2:12][CH2:13]4)[CH3:2]

Participants

5

Reactant 2

HCID 68576452HCID 68576452, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 68576999HCID 68576999, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 3-vinyl-N-(tert-butyloxycarbonyl)morphinan, 44 (10 mg, 0.028 mmol) in dry methanol (1 mL) was added Pd/C (4 mg) and the flask was charged with hydrogen gas in a balloon. After starting material disappeared on TLC, solvent was evaporated and column chromatography of the residue gave 7 mg (70%) of product: 1H NMR (300 MHz, CDCl3) δ7.06˜7.36 (3H, m); 4.37 (0.5H, s); 4.19 (0.5H, s); 3.88 (1H, dd); 3.11 (1H, m); 2.63 (2H, m); 2.59 (2H, m); 2.44 (1H, m); 1.60˜1.80 (4H, m); 1.40˜1.60 (9H, d); 0.90˜1.40 (9H, m).

Workup

  1. customwas evaporated

Sources & evidence

ORD record
ord-27b3e54682494d9eaf0cb601ab0a71e3
Source dataset
uspto-grants-2010_04
Patent number
US07691874B2

Reaction notes

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