HCID 59402251, compound → (S)-Methyl-pyrrolidin-3-yl-carbamic acid tert-butyl ester

HRID 338855Notes

Reaction equation

HRID 338855 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:24])[C@H:9]1[CH2:13][CH2:12][N:11](C(OCC2C=CC=CC=2)=O)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.CO.[Pd]>[CH3:24][N:8]([C@H:9]1[CH2:13][CH2:12][NH:11][CH2:10]1)[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 59402251HCID 59402251, compound

Product 1

HCID 7171888(S)-Methyl-pyrrolidin-3-yl-carbamic acid tert-butyl esterYield 99.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a suspension of 5% Pd/C (4.60 g, 2.16 mmol) in ethanol (40 mL) was added slowly a solution of (S)-benzyl 3-(tert-butoxycarbonyl(methyl)amino)pyrrolidine-1-carboxylate (7.2 g, 21.6 mmol) in methanol (20 mL). The mixture was evacuated and backfilled with nitrogen and then evacuated and backfilled with hydrogen then stirred under a hydrogen atmosphere for 2 hours. The suspension was filtered through a pad of Celite and washed with methanol (60 mL). The filtrate was concentrated under reduced pressure to afford (S)-tert-butyl methyl(pyrrolidin-3-yl)carbamate (4.3 g, 99%).

Workup

  1. customThe mixture was evacuated
  2. customevacuated
  3. filtrationThe suspension was filtered through a pad of Celite
  4. washwashed with methanol (60 mL)
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f15e3f0e15554274a9d6feb005bbd7be
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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