Cyclohexanone → HCID 68503869, compound

HRID 1176569Notes

Reaction equation

HRID 1176569 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:11]2[CH:12]=[C:13]([CH2:16][O:17][CH:18]3[CH:23]([C:24]4[CH:29]=[CH:28][C:27]([O:30][C@H:31]5[CH2:35][CH2:34][NH:33][CH2:32]5)=[CH:26][CH:25]=4)[CH2:22][CH2:21][N:20]([C:36]([O:38][CH2:39][C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[O:37])[CH2:19]3)[CH:14]=[CH:15][C:10]=2[O:9][CH2:8][C:7]1=[O:46].[C:47]1(=O)[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[CH:47]1([N:33]2[CH2:34][CH2:35][C@H:31]([O:30][C:27]3[CH:26]=[CH:25][C:24]([CH:23]4[CH2:22][CH2:21][N:20]([C:36]([O:38][CH2:39][C:40]5[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=5)=[O:37])[CH2:19][CH:18]4[O:17][CH2:16][C:13]4[CH:14]=[CH:15][C:10]5[O:9][CH2:8][C:7](=[O:46])[N:6]([CH2:5][CH2:4][CH2:3][O:2][CH3:1])[C:11]=5[CH:12]=4)=[CH:29][CH:28]=3)[CH2:32]2)[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]1

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 5049666Sodium triacetoxyborohydrideHCID 68502007HCID 68502007, compound

Product 1

HCID 68503869HCID 68503869, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 0.374 g of benzyl 3-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-4-[4-(pyrrolidin-3(S)-yloxy)phenyl]piperidine-1-carboxylate is admixed under argon with 0.038 ml of acetic acid and 0.078 ml of cyclohexanone. 0.199 g of sodium triacetoxyborohydride is added in portions at room temperature to this reaction solution and the reaction mixture is subsequently stirred at room temperature over one hour. The reaction mixture is concentrated by evaporation and the residue is taken up in 20 ml of ethyl acetate. The organic solution is washed with 10 ml each of saturated aqueous sodium hydrogencarbonate solution and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a colourless resin from the residue by means of flash chromatography (SiO2 60F). Rf=0.20 (200:20:1 dichloromethane-methanol-25% conc. ammonia); Rt=4.52.

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. washThe organic solution is washed with 10 ml each of saturated aqueous sodium hydrogencarbonate solution and brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-793cf6745faa4755ba4272e3e196bc9b
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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