Tributylstannane → HCID 21309366, compound

HRID 1075546Notes

Reaction equation

HRID 1075546 reaction equation
[C:1]([O:5][C@H:6]1[CH2:15][CH2:14][CH2:13][C:12]2[C@:7]1([CH3:24])[CH2:8][CH2:9][C@H:10](OC(N1C=CN=C1)=S)[CH:11]=2)([CH3:4])([CH3:3])[CH3:2].C([SnH](CCCC)CCCC)CCC.C(B(CC)CC)C>C1(C)C=CC=CC=1.O1CCCC1>[C:1]([O:5][C@@H:6]1[C@:7]2([CH3:24])[C:12](=[CH:11][CH2:10][CH2:9][CH2:8]2)[CH2:13][CH2:14][CH2:15]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 5948Tributylstannane2×HCID 7357Triethylborane2×HCID 20638409HCID 20638409, compound

Product 1

HCID 21309366HCID 21309366, compoundYield 67.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 9.95 g (28.5 mMol) imidazole-1-carbothioic acid(2S, 4aS, 5S)-O-(5-tert-butoxy-4a-methyl-2,3,4,4a,5,6,7,8-octahydro-naphtalen -2-yl)ester in 285 ml toluene kept under argon atmosphere were added 75.7 ml (285 mMol) of tributyltinhydride and 75.7 ml of a one molar solution of triethylborane in tetrahydrofuran. The reaction mixture was heated to 120° C. for 4 hours and additional 20 ml of tributyltinhydride as well as 20 ml of triethylborane solution (one molar in tetrahydrofuran) were added. The reaction mixture was kept at 120° C. for 3 days, cooled to room temperature and evaporated in vacuo. The residue was chromatographed twice over 900 g silica gel with toluene/hexane 1/1 to yield 4.3 g of pure (4S,4aS)-4-tert-Butoxy-4a-methyl-1,2,3,4,4a,5,6,7-octahydro-naphtalene (liquid).

Workup

  1. temperaturecooled to room temperature
  2. customevaporated in vacuo
  3. customThe residue was chromatographed twice over 900 g silica gel with toluene/hexane 1/1

Sources & evidence

ORD record
ord-468f019ff4724886a87e840467ceed7a
Source dataset
uspto-grants-1999_05
Patent number
US05905074

Reaction notes

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