Water → HCID 131718449, compound

HRID 1109188Notes

Reaction equation

HRID 1109188 reaction equation
[CH:1]1([CH2:7][N:8]2[C@@H:16]3[C@@H:11]([C:12]4[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[C:13]=4[CH2:14][CH2:15]3)[CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:22]([N:24]([CH2:27]C)[CH2:25]C)C.CC(N(C)Cl)=[O:31].O>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH3:22][N:24]([CH3:27])[C:25](=[O:31])[O:21][C:17]1[C:13]2[CH2:14][CH2:15][C@H:16]3[C@H:11]([CH2:10][CH2:9][N:8]3[CH2:7][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[C:12]=2[CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 12663100HCID 12663100, compoundHCID 131718448HCID 131718448, compound

Product 1

HCID 131718449HCID 131718449, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

2.78 g (0.00973 mol) of rac-cis-3-cyclohexylmethyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-ol were dissolved in 50 ml of toluene. 1.97 g (2.71 ml, 0.01948 mol) of triethylamine and 120 mg (980 mmol, 0.1 eq.) of 4-dimethylaminopyridine were added thereto in succession and then 1.79 ml (0.01948 mol) of dimethyl chloroformamide were added dropwise thereto. The mixture was boiled under reflux for 2 hours, then cooled, poured into water and extracted with toluene. The organic phase was washed with water, dried with Na2SO4, filtered and concentrated. By chromatography of the residue over 220 g of silica gel with cyclohexane/ethyl acetate 1:1 there were obtained 3.3 g (95%) of oily rac-cis-3-cyclohexylmethyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-yl dimethylcarbamate.

Workup

  1. temperatureunder reflux for 2 hours
  2. temperaturecooled
  3. extractionextracted with toluene
  4. washThe organic phase was washed with water
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-935006c29dea4ead87a990e9dfcebd6a
Source dataset
uspto-grants-1994_06
Patent number
US05318967

Reaction notes

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