Borane;tetrahydrofuran → HCID 67061811, compound

HRID 910809Notes

Reaction equation

HRID 910809 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)=[O: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][CH2:48][OH:49])[CH2:15]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 67061895HCID 67061895, compound

Product 1

HCID 67061811HCID 67061811, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1.0 mmol of [(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]-acetic acid (example 1g) in 4 ml of THF are added 2.2 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 residue is purified 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 residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-f16dba4610424db1906dc24d74ae2f3c
Source dataset
uspto-grants-2011_09
Patent number
US08022068B2

Reaction notes

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