HCID 57300086, compound → tert-Butyl (2R,4S)-4-amino-2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 1740477Notes

Reaction equation

HRID 1740477 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][O:17]C(C1C=CC=CC=1)(C1C=CC(OC)=CC=1)C1C=CC(OC)=CC=1)=[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 57300086HCID 57300086, compound

Product 1

HCID 44828601tert-Butyl (2R,4S)-4-amino-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(2R,4S)-1-(tert-Butyloxycarbonyl)-2-(4,4'-Dimethoxytrityl)oxymethyl-4-azido-pyrrolidine 40 (2.72 g, 5 mmol) in methanol (75 ml) was hydrogenated in the presence of 10% palladium on charcoal (0.3 g) at room temperature and 5 atm pressure. After 12 h, the catalyst was filtered, washed with methanol (20 ml) and the solvent removed under vacuum. Yield 1.0 g (93%). 1HNMR (CDCl3): 1.45 (s, 9H, Boc), 1.90 (dd, 1H), 2.34 (m, 1H), 3.40-3.62 (m, 3H), 4.00 (m, 2H), 4.28 (bs, 1H) and 4.44 (m, 1H).

Workup

  1. filtrationthe catalyst was filtered
  2. washwashed with methanol (20 ml)
  3. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-184223cbf0914c5c92077bbf39fa2c08
Source dataset
uspto-grants-1999_10
Patent number
US05969135

Reaction notes

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