rel-(1S,2R,5S)-2-azido-5-(tert-butyl(diphenyl)silyl)oxy-1-methyl-cyclopentanol → rel-(1S,2R,5S)-2-Amino-5-(tert-butyl(diphenyl)silyl)oxy-1-methyl-cyclopentanol

HRID 245067Notes

Reaction equation

HRID 245067 reaction equation
[N:1]([C@@H:4]1[CH2:8][CH2:7][C@H:6]([O:9][Si:10]([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C@@:5]1([CH3:28])[OH:27])=[N+]=[N-]>[Pd].C(O)C>[NH2:1][C@@H:4]1[CH2:8][CH2:7][C@H:6]([O:9][Si:10]([C:23]([CH3:25])([CH3:24])[CH3:26])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@:5]1([CH3:28])[OH:27]

Participants

4

Reactant 1

HCID 86693778rel-(1S,2R,5S)-2-azido-5-(tert-butyl(diphenyl)silyl)oxy-1-methyl-cyclopentanol

Product 1

HCID 86693777rel-(1S,2R,5S)-2-Amino-5-(tert-butyl(diphenyl)silyl)oxy-1-methyl-cyclopentanolYield 20%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of rel-(1S,2R,5S)-2-azido-5-(tert-butyl(diphenyl)silyl)oxy-1-methyl-cyclopentanol (2.28 g, 5.76 mmol, enantiomeric mixture) and 10% palladium on carbon (61 mg) in ethanol (29 mL) is hydrogenated (60 psi) at room temperature for 16 h. The reaction is filtered through a pad of diatomaceous earth and rinsed with EtOH (50 mL). The filtrate is concentrated in vacuo, dissolved in dichloromethane (10 mL), and concentrated in vacuo. The crude product is purified on silica gel (120 g, 1-6% (2 M ammonia in methanol/dichloromethane) to afford the title compound as an opaque yellow oil (419 mg, 20%). LC-ES/MS m/z 353 (M+1).

Workup

  1. customat room temperature
  2. customfor 16 h
  3. filtrationThe reaction is filtered through a pad of diatomaceous earth
  4. washrinsed with EtOH (50 mL)
  5. concentrationThe filtrate is concentrated in vacuo
  6. dissolutiondissolved in dichloromethane (10 mL)
  7. concentrationconcentrated in vacuo
  8. customThe crude product is purified on silica gel (120 g, 1-6% (2 M ammonia in methanol/dichloromethane)

Sources & evidence

ORD record
ord-b97ab8e8c7bb43a68dfd9e2deeb76cf8
Source dataset
uspto-grants-2014_02
Patent number
US08658693B2

Reaction notes

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