(2R,4R)-4-Azido-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester → tert-butyl (2R,4R)-4-amino-2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 244350Notes

Reaction equation

HRID 244350 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([N:13]=[N+]=[N-])[CH2:10][C@@H:9]1[CH2:16][OH:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([NH2:13])[CH2:10][C@@H:9]1[CH2:16][OH:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 58564434(2R,4R)-4-Azido-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 45072438tert-butyl (2R,4R)-4-amino-2-(hydroxymethyl)pyrrolidine-1-carboxylateYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Hydrogenate a mixture of (2R,4R)-4-azido-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (225 g, 0.93 mol) and 10% palladium on carbon (22.5 g, pre-wetted with toluene) in methanol (2.3 L) at 15 psi of hydrogen at room temperature for 16 h. Filter off the catalyst and concentrate the filtrate to obtain the title compound as an oil (198 g, 92%). 1H NMR (400 MHz, DMSO-d6) δ 1.38 (s, 9H), 1.58 (m, 1H), 2.16 (m, 1H), 2.95 (m, 1H), 3.20-3.58 (m, 6H), 3.61 (m, 1H), 3.65 (br s, 1H).

Workup

  1. filtrationFilter off the catalyst
  2. concentrationconcentrate the filtrate

Sources & evidence

ORD record
ord-7fb19b96761747ba93f21083070bb514
Source dataset
uspto-grants-2014_02
Patent number
US08658638B2

Reaction notes

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