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

HRID 1292205Notes

Reaction equation

HRID 1292205 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

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 4N 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. temperatureheated at 80°-90° C. for 4 hours under an argon atmosphere
  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-00f7753c137d40f0a5a0bc77779be696
Source dataset
uspto-grants-1998_05
Patent number
US05756532

Reaction notes

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