HCID 13008958, compound → tert-Butyl (2S,4S)-4-amino-2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 1670612Notes

Reaction equation

HRID 1670612 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]>CO.[Pd]>[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

4

Reactant 1

HCID 13008958HCID 13008958, compound

Product 1

HCID 44828599tert-Butyl (2S,4S)-4-amino-2-(hydroxymethyl)pyrrolidine-1-carboxylateYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Dissolve (2S,4S)-4-azido-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (32 g) in methanol (150 mL). Add 10% palladium on carbon (3.2 g) and hydrogenate (1 atm) at room temperature for 16 h. Filter off the catalyst through a plug of diatomaceous earth and concentrate under vacuum to obtain the title compound (28 g, crude) as a thick, yellow oil.

Workup

  1. filtrationFilter off the catalyst through a plug of diatomaceous earth
  2. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-2d2d1084c0ec4473afb12c6726d63fb9
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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