Ethanolamine → Benzyl 4-(4-{[2-(2,5-difluorophenoxy)ethylamino]methyl}phenyl)-3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate

HRID 1712542Notes

Reaction equation

HRID 1712542 reaction equation
[F:1][C:2]1[CH:53]=[CH:52][C:51]([F:54])=[CH:50][C:3]=1[O:4][CH2:5][CH2:6][NH:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[CH2:18][CH:17]2[O:32][CH2:33][C:34]2[CH:35]=[CH:36][C:37]3[O:42][CH2:41][C:40](=O)[N:39]([CH2:44][CH2:45][CH2:46][O:47][CH3:48])[C:38]=3[CH:49]=2)=[CH:12][CH:11]=1)=O.B1C2CCCC1CCC2.C(CN)O>O1CCCC1>[F:1][C:2]1[CH:53]=[CH:52][C:51]([F:54])=[CH:50][C:3]=1[O:4][CH2:5][CH2:6][NH:7][CH2:8][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[O:23])[CH2:18][CH:17]2[O:32][CH2:33][C:34]2[CH:35]=[CH:36][C:37]3[O:42][CH2:41][CH2:40][N:39]([CH2:44][CH2:45][CH2:46][O:47][CH3:48])[C:38]=3[CH:49]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 789669-Borabicyclo(3.3.1)nonaneHCID 68500755HCID 68500755, compound

Product 1

HCID 68500812Benzyl 4-(4-{[2-(2,5-difluorophenoxy)ethylamino]methyl}phenyl)-3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The solution of 0.440 g of benzyl 4-{4-[2-(2,5-difluorophenoxy)ethylcarbamoyl]phenyl}-3-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate in 2.0 ml of tetrahydrofuran is admixed with 13.6 ml of 9-BBN (0.5M in tetrahydrofuran) and stirred at reflux over 18 hours. The reaction mixture is cooled, admixed with 0.412 ml of ethanolamine and concentrated by evaporation. The residue is stirred at 0° C. in 40 ml of EtOAc-heptane (1:1) overnight and clarified by filtration, and the filtrate is concentrated by evaporation. The title compound is obtained as a slightly yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.11 (1:3 EtOAc-heptane); Rt=4.76.

Workup

  1. temperatureat reflux over 18 hours
  2. temperatureThe reaction mixture is cooled
  3. concentrationconcentrated by evaporation
  4. stirringThe residue is stirred at 0° C. in 40 ml of EtOAc-heptane (1:1) overnight
  5. filtrationclarified by filtration
  6. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-108f63fcd3344ecbb99628994af72b34
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

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