1,1-Dimethylethyl (3R)-3-[[(phenylmethoxy)carbonyl]amino]-1-pyrrolidinecarboxylate → (R)-(+)-1-Boc-3-aminopyrrolidine

HRID 1829886Notes

Reaction equation

HRID 1829886 reaction equation
C(OC([NH:11][C@@H:12]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13]1)=O)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:11][C@@H:12]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13]1

Participants

4

Reactant 1

HCID 115370521,1-Dimethylethyl (3R)-3-[[(phenylmethoxy)carbonyl]amino]-1-pyrrolidinecarboxylate

Product 1

HCID 854070(R)-(+)-1-Boc-3-aminopyrrolidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(R)-3-(Benzyloxycarbonylamino)-N-(t-butoxycarbonyl)-pyrrolidine (300 mg) was dissolved in ethanol (5 ml). Palladium on charcoal 10% (20 mg) was added. The reaction was degassed three times and put under hydrogen atmosphere (1 bar). The reaction was over after 2 hours. The solvent was removed, the residue was taken up in ethyl acetate (5 ml) and filtered through a silica gel pad. The silica was washed with ethyl acetate (50 ml). The organic phases were evaporated. The desired (R)-3-Amino-N-(t-butoxycarbonyl)-pyrrolidine was obtained as a colorless oil in a quantitative yield (175 mg).

Workup

  1. customThe reaction was degassed three times
  2. customafter 2 hours
  3. customThe solvent was removed
  4. filtrationfiltered through a silica gel pad
  5. washThe silica was washed with ethyl acetate (50 ml)
  6. customThe organic phases were evaporated

Sources & evidence

ORD record
ord-f62245dd0989491f918be9cc74897f83
Source dataset
uspto-grants-2006_06
Patent number
US07064199B2

Reaction notes

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