Potassium Cyanide → HCID 86751023, compound

HRID 263817Notes

Reaction equation

HRID 263817 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[CH:40]=[CH:39][CH:38]=[CH:37][C:12]=1[O:13][C:14]1[CH:15]=[CH:16][C:17](Br)=[C:18]2[C:23]=1[CH2:22][C@:21]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])([C:24]([O:26][CH3:27])=[O:25])[CH2:20][CH2:19]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:41]#[N:42].[K+]>CN(C)C(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([O:8][C:9]([C:11]1[CH:40]=[CH:39][CH:38]=[CH:37][C:12]=1[O:13][C:14]1[CH:15]=[CH:16][C:17]([C:41]#[N:42])=[C:18]2[C:23]=1[CH2:22][C@:21]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])([C:24]([O:26][CH3:27])=[O:25])[CH2:20][CH2:19]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 86751024HCID 86751024, compound

Product 1

HCID 86751023HCID 86751023, compoundYield 8.6%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 66545394HCID 66545394, compoundCatalystHCID 31374DimethylacetamideSolvent

Procedure

A mixture of 90.0 mg (0.147 mmol) of methyl (S)-8-(2-benzyloxycarbonyl-phenoxy)-5-bromo-2-(tert.butoxycarbonylamino)-1,2,3,4-tetrahydro-naphthalene-2-carboxylate, 19.2 mg (0.295 mmol) of potassium cyanide, 6.5 mg (11.8 μmol) of 1,1'-bis-(diphenylphosphino)-ferrocene and 3,0 mg (2.9 μmol) of bis-(dibenzylideneacetone)-di-palladium (Pd2 dba3) in 0.2 ml of N,N-dimethylacetamide was stirred at 800 under argon for 15 hours, cooled and filtered over Celite, whereupon the filtrate was evaporated. The residue was chromatographed on 30 g of silica gel with hexane/ethyl acetate (9:1→1:1), whereby firstly 71 mg (78.9%) of starting material were recovered; subsequently there were obtained about 7.0 mg (8.6%) of crude methyl (S)-8-(2-benzyloxycarbonyl-phenoxy)-2-(tert.butoxycarbonylamino)-5-cyano-1,2,3,4-tetrahydro-naphthalene-2-carboxylate which was purified by means of preparative HPLC chromatography (column: Vydac 250-10 RP-18; programme: 60% acetonitrile→100% acetonitrile in 20 minutes). 5.5 mg (6.7% based on starting material used; 31.6% based on reacted starting product) of pure product were obtained. MS: 556 (M+., <1), 439 (10), 397 (20), 91 (100), 57 (24).

Workup

  1. temperaturecooled
  2. filtrationfiltered over Celite, whereupon the filtrate
  3. customwas evaporated
  4. customThe residue was chromatographed on 30 g of silica gel with hexane/ethyl acetate (9:1→1:1), whereby firstly 71 mg (78.9%) of starting material
  5. customwere recovered

Sources & evidence

ORD record
ord-6e914194bc454679a6c2e7d730bcf503
Source dataset
uspto-grants-1997_07
Patent number
US05644024

Reaction notes

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