Tricyclo(3.3.1.13,7)dec-1-ylmethylamine → HCID 10475248, compound

HRID 1737422Notes

Reaction equation

HRID 1737422 reaction equation
C1(C)C=CC(S(O[CH2:11][C@@H:12]2[O:26][C:16]3=[C:17]4[C:21](=[C:22]([F:24])[CH:23]=[C:15]3[O:14][CH2:13]2)[NH:20][C:19](=[O:25])[CH2:18]4)(=O)=O)=CC=1.[C:28]12([CH2:38][NH2:39])[CH2:37][CH:32]3[CH2:33][CH:34]([CH2:36][CH:30]([CH2:31]3)[CH2:29]1)[CH2:35]2>CS(C)=O.C(OCC)(=O)C.CCCCCC>[C:28]12([CH2:38][NH:39][CH2:11][CH:12]3[O:26][C:16]4=[C:17]5[C:21](=[C:22]([F:24])[CH:23]=[C:15]4[O:14][CH2:13]3)[NH:20][C:19](=[O:25])[CH2:18]5)[CH2:35][CH:34]3[CH2:33][CH:32]([CH2:31][CH:30]([CH2:36]3)[CH2:29]1)[CH2:37]2

Participants

5

Reactant 2

HCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamineHCID 18660183HCID 18660183, compound

Product 1

HCID 10475248HCID 10475248, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
85 °C

Procedure

(R)-2-(Toluene-4-sulfonyloxymethyl)-6-fluoro-2,3,8,9-tetrahydro-7H-1,4-dioxino[2,3-e]indol-8-one (1.0 g, 2.5 mmole) and 1-adamantylmethylamine (1.6 g, 10 mmole) were combined in 30 ml of dry DMSO and heated at 80-90° C. for 4 hours under an argon atmosphere. After cooling to room temperature, the mixture was diluted with 500 ml of 1:1 ethyl acetate/hexane and washed with 250 ml of saturated aqueous sodium bicarbonate and with two 250 ml portions of water, dried over sodium sulfate, filtered and concentrated in vacuum. The residue was column chromatographed on silica gel using 0.5% methanol/CHCl3 as eluant to give 0.70 g of the free base of the title compound as a colorless oil. This was crystallized from ethanol with the addition 4 N isopropanolic HCl to give 0.54 g of the (S) enantiomer of the title compound as a fluffy white solid hydrochloride, m.p.>260° C.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with 250 ml of saturated aqueous sodium bicarbonate and with two 250 ml portions of water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customchromatographed on silica gel using 0.5% methanol/CHCl3 as eluant

Sources & evidence

ORD record
ord-b90b0b5068904a9b87130e1c802c8e00
Source dataset
uspto-grants-1999_10
Patent number
US05962465

Reaction notes

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