({(1S,2S,4R)-4-azido-2-[(benzyloxy)methyl]cyclopentyl}-oxy)(tert-butyl)dimethylsilane → (1R,3S,4S)-3-[(benzyloxy)methyl]-4-{[tert-butyl(dimethyl)-silyl]oxy}cyclopentanamine

HRID 447612Notes

Reaction equation

HRID 447612 reaction equation
[N:1]([C@H:4]1[CH2:8][C@H:7]([O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[C@H:6]([CH2:17][O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:5]1)=[N+]=[N-]>CCOC(C)=O.[Pd]>[CH2:19]([O:18][CH2:17][C@H:6]1[C@@H:7]([O:9][Si:10]([C:13]([CH3:15])([CH3:14])[CH3:16])([CH3:12])[CH3:11])[CH2:8][C@H:4]([NH2:1])[CH2:5]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 1

HCID 86618712({(1S,2S,4R)-4-azido-2-[(benzyloxy)methyl]cyclopentyl}-oxy)(tert-butyl)dimethylsilane

Product 1

HCID 66798113(1R,3S,4S)-3-[(benzyloxy)methyl]-4-{[tert-butyl(dimethyl)-silyl]oxy}cyclopentanamineYield 98.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of ({(1S,2S,4R)-4-azido-2-[(benzyloxy)methyl]cyclopentyl}-oxy)(tert-butyl)dimethylsilane (2.20 g, 0.00608 mol) and 10% Pd/C (0.16 g, 0.00015 mol) in EtOAc (23.9 mL) was stirred under an atmosphere of hydrogen overnight. The reaction was purged with nitrogen and the mixture filtered through celite with EtOAc. The filtrate was concentrated to obtain 2.01 g (98%) of the title compound.

Workup

  1. customThe reaction was purged with nitrogen
  2. filtrationthe mixture filtered through celite with EtOAc
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-aa9525c24e744a068fc343d194a8d4b1
Source dataset
uspto-grants-2013_07
Patent number
US08481550B2

Reaction notes

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