Lithium borohydride → (R)-1-(3-(Hydroxymethyl)-2,3-dihydro-1,2,4-oxadiazol-5-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethyl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate

HRID 2099840Notes

Reaction equation

HRID 2099840 reaction equation
[BH4-].[Li+].[O:3]=[C:4]1[C:13]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C@@H:23]([C:43]3[O:47][N:46]=[C:45]([C:48](OCC)=[O:49])[N:44]=3)[CH2:24][C:25]3[CH:33]=[C:32]([CH3:34])[C:31]4[C:27](=[CH:28][N:29]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[N:30]=4)[CH:26]=3)=[O:21])[CH2:16][CH2:15]2)=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5]1>C(O)C>[O:3]=[C:4]1[C:13]([CH:14]2[CH2:15][CH2:16][N:17]([C:20]([O:22][C@@H:23]([C:43]3[O:47][NH:46][CH:45]([CH2:48][OH:49])[N:44]=3)[CH2:24][C:25]3[CH:33]=[C:32]([CH3:34])[C:31]4[C:27](=[CH:28][N:29]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:40])([CH3:42])[CH3:41])[N:30]=4)[CH:26]=3)=[O:21])[CH2:18][CH2:19]2)=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5]1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 57794676(R)-1-(3-(Ethoxycarbonyl)-1,2,4-oxadiazol-5-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethyl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate

Product 1

HCID 69076113(R)-1-(3-(Hydroxymethyl)-2,3-dihydro-1,2,4-oxadiazol-5-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethyl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Solid lithium borohydride (1.5 mg, 0.0689 mmol) was added to a stirred solution of (R)-1-(3-(ethoxycarbonyl)-1,2,4-oxadiazol-5-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethyl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate (2.3 mg, 0.00328 mmol) in ethanol (2 mL) at room temperature. The mixture was stirred for 3 h, and then quenched with saturated ammonium chloride and extracted with methylene chloride (15 mL). The organic layer was washed with brine (5 mL), dried over magnesium sulfate, and concentrated in vacuo to afford the expected product (2.02 mg, 94%).

Workup

  1. customquenched with saturated ammonium chloride
  2. extractionextracted with methylene chloride (15 mL)
  3. washThe organic layer was washed with brine (5 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c7daa4aef4744c6593c76e22840e453d
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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