tert-butyl (3S,4S)-3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate → 1-Boc-(3S,4S)-3-amino-4-hydroxypyrrolidine

HRID 1670618Notes

Reaction equation

HRID 1670618 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[C@@H:10]([NH:14]CC2C=CC=CC=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)CCC.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[C@@H:10]([NH2:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 11277777tert-butyl (3S,4S)-3-(benzylamino)-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 104654571-Boc-(3S,4S)-3-amino-4-hydroxypyrrolidineYield 101.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 2631-ButanolSolvent

Procedure

To a solution of (3S,4S)-3-benzylamino-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (0.054 mol, 16.0 g) in n-butanol (225 mL) add 10% Pd/C (5.0 g) and hydrogenate the mixture at 50 psi for 10 h. Filter the reaction mixture thorough a plug of diatomaceous earth and wash with ethanol. Evaporate the filtrate to obtain the title compound as a white solid (11.10 g, 99%). APCI MS m/z 203 [M+H]+; [α]23D +7.8° (c, 0.50, MeOH).

Workup

  1. filtrationFilter the reaction mixture thorough a plug of diatomaceous earth
  2. washwash with ethanol
  3. customEvaporate the filtrate

Sources & evidence

ORD record
ord-dba5d7cbccb1442f95d9a897d4448397
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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