trans-3-Azido-1-Boc-4-hydroxypyrrolidine → 1-Boc-(3S,4S)-3-amino-4-hydroxypyrrolidine

HRID 1162632Notes

Reaction equation

HRID 1162632 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[C@@H:10]([N:14]=[N+]=[N-])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>O=[Pt]=O.CO>[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 11128048trans-3-Azido-1-Boc-4-hydroxypyrrolidine

Product 1

HCID 104654571-Boc-(3S,4S)-3-amino-4-hydroxypyrrolidineYield 84.6%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

22.3 A solution of 2.0 g (3S,4S)-3-azido-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester in 25 MeOH was treated under an argon atmosphere with 100 mg PtO2. The reaction mixture was stirred over night under a hydrogen atmosphere. The catalyst was filtered off and washed with methanol. The filtrate was concentrated. The crude product was purified by chromatography (silica gel; gradient: CH2Cl2->CH2Cl2/MeOH 4:1) to give 1.5 g (3S,4S)-3-amino-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester as off-white solid. MS 202.9 ([M+H]+)

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated
  4. customThe crude product was purified by chromatography (silica gel; gradient: CH2Cl2->CH2Cl2/MeOH 4:1)

Sources & evidence

ORD record
ord-cd973992864842339a5f6af37e37660b
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

Loading…