Aluminium lithium hydride → tert-Butyl 4-[({[2-{[tert-butyl(diphenyl)silyl]oxy}-1-(hydroxymethyl)ethyl]amino}carbonyl)amino]piperidine-1-carboxylate

HRID 1867598Notes

Reaction equation

HRID 1867598 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([NH:20][C:21]([NH:23][C@H:24]([C:44](O)=[O:45])[CH2:25][O:26][Si:27]([C:40]([CH3:43])([CH3:42])[CH3:41])([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:22])[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>O1CCCC1>[Si:27]([O:26][CH2:25][CH:24]([NH:23][C:21]([NH:20][CH:17]1[CH2:16][CH2:15][N:14]([C:12]([O:11][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:13])[CH2:19][CH2:18]1)=[O:22])[CH2:44][OH:45])([C:40]([CH3:41])([CH3:42])[CH3:43])([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68825752N-({[1-(tert-butoxycarbonyl)piperidin-4-yl]amino}carbonyl)-O-[tert-butyl(diphenyl)silyl]serine

Product 1

HCID 68568228tert-Butyl 4-[({[2-{[tert-butyl(diphenyl)silyl]oxy}-1-(hydroxymethyl)ethyl]amino}carbonyl)amino]piperidine-1-carboxylateYield 28.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (1 M, 0.703 mL, 0.703 mmol) was added to a solution of N-({[1-(tert-butoxycarbonyl)piperidin-4-yl]amino}carbonyl)-O-[tert-butyl(diphenyl)silyl]serine (373 mg, 0.639 mmol) in tetrahydrofuran (20 mL) at −78° C. The reaction was quenched with saturated ammonium chloride solution and partitioned between dichloromethane and saturated sodium bicarbonate solution. The organic layer was dried over sodium sulfate, filtered, and concentrated. Purification by silica gel chromatography (1%→8% methanol {1% ammonium hydroxide}/dichloromethane) gave the title compound (100 mg). MS 556.3 (M+1)

Workup

  1. customThe reaction was quenched with saturated ammonium chloride solution
  2. custompartitioned between dichloromethane and saturated sodium bicarbonate solution
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (1%→8% methanol {1% ammonium hydroxide}/dichloromethane)

Sources & evidence

ORD record
ord-1664be202c574ce39031fc0b2645b5a9
Source dataset
uspto-grants-2009_12
Patent number
US07632832B2

Reaction notes

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