Borane;tetrahydrofuran → HCID 67061772, compound

HRID 910798Notes

Reaction equation

HRID 910798 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]([CH3:51])[CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]2[C@@H:19]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]4[O:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][CH2:33][O:34][CH3:35])[C:26]=4[CH:36]=3)[CH2:18][N:17]([S:37]([C:40]3[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=3)(=[O:39])=[O:38])[C@@H:16]([CH2:47][C:48](=[O:50])[CH3:49])[CH2:15]2)=[CH:10][CH:9]=1.O1CCCC1.B>C1COCC1>[CH3:1][O:2][CH2:3][C@H:4]([CH3:51])[CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]2[C@@H:19]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]4[O:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][CH2:33][O:34][CH3:35])[C:26]=4[CH:36]=3)[CH2:18][N:17]([S:37]([C:40]3[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=3)(=[O:38])=[O:39])[C@@H:16]([CH2:47][C@@H:48]([OH:50])[CH3:49])[CH2:15]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 67061816HCID 67061816, compound

Product 1

HCID 67061772HCID 67061772, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1.0 mmol of 1-[(2R,4R,5R)-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-propan-2-one in 10 ml of THF are added 2.0 mmol of borane tetrahydrofuran complex (1M in THF) at RT. The reaction mixture is stirred for 3 h, quenched with 60 ml of MeOH and concentrated under reduced pressure. The resulting diastereomeric mixture is separated by flash chromatography (SiO2 60 F) to afford the title compound which is identified based on its Rf-value.

Workup

  1. customquenched with 60 ml of MeOH
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting diastereomeric mixture is separated by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-a3ad4900aac94ecab11bd5c873ea83eb
Source dataset
uspto-grants-2011_09
Patent number
US08022068B2

Reaction notes

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