HCID 131720085, compound → HCID 131720084, compound

HRID 263818Notes

Reaction equation

HRID 263818 reaction equation
C(OC([NH:11][C@:12]1([C:36]([O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])=[O:37])[CH2:21][C:20]2[C:19]([O:22][C:23]3([CH:35]=[CH:34][CH:33]=[N:32][CH2:31]3)[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:14][CH2:13]1)=O)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:11][C@:12]1([C:36]([O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])=[O:37])[CH2:21][C:20]2[C:19]([O:22][C:23]3([CH:35]=[CH:34][CH:33]=[N:32][CH2:31]3)[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:14][CH2:13]1

Participants

4

Reactant 1

HCID 131720085HCID 131720085, compound

Product 1

HCID 131720084HCID 131720084, compoundYield 81.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 298 mg (0.48 mmol) of tert.-butyl 3-[(S)-7-benzyloxycarbonylamino-7-trimethylsilylethoxycarbonyl-5,6,7,8-tetrahydro-naphthalen-1-yloxy]nicotinate in 5 ml of ethanol was hydrogenated under a hydrogen atmosphere with 80 mg of palladium-charcoal (10%) at room temperature for 1 hour, whereupon the mixture was filtered over Hyflo and the filtrate was concentrated. The residue was dried in a high vacuum and chromatographed on 50 g of silica gel with chloroform/methanol (95:5), whereupon 190 mg (81.7%) of tert.-butyl 3-[(S)-7-amino-7-trimethylsilylethoxycarbonyl-5,6,7,8-tetrahydro-naphthalen-1-yloxy]-nicotinate were obtained. MS (ISP): 485.5 (M+. +H+, 50), 429 (15), 401.3 (100).

Workup

  1. filtrationwas filtered over Hyflo
  2. concentrationthe filtrate was concentrated
  3. customThe residue was dried in a high vacuum
  4. customchromatographed on 50 g of silica gel with chloroform/methanol (95:5)

Sources & evidence

ORD record
ord-f3b87fa12e594bdd96841db41ef03169
Source dataset
uspto-grants-1997_07
Patent number
US05644024

Reaction notes

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