benzyl (3R,4R)-3-((tert-butoxycarbonyl)amino)-4-hydroxypyrrolidine-1-carboxylate → (4-Hydroxy-pyrrolidin-3-yl)-carbamic acid tert-butyl ester

HRID 1398021Notes

Reaction equation

HRID 1398021 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[C@H:13]([OH:14])[CH2:12][N:11](C(OCC2C=CC=CC=2)=O)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]1[CH:13]([OH:14])[CH2:12][NH:11][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 59640637benzyl (3R,4R)-3-((tert-butoxycarbonyl)amino)-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 67437029(4-Hydroxy-pyrrolidin-3-yl)-carbamic acid tert-butyl esterYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A racemic mixture of trans-benzyl 3-(tert-butoxycarbonylamino)-4-hydroxypyrrolidine-1-carboxylate (3.36 g, 9.99 mmol) (Method 190) in MeOH (40 mL) was degassed, then 10 wt % Pd/C (3.19 g, 3.00 mmol) was added. The mixture was degassed, charged with H2, and stirred overnight. The mixture was filtered through a bed of Celite, washed with methanol, the filtrate was dried over anhydrous Na2SO4, filtered and conc. in vacuo to yield a white solid as racemic tert-butyl-4-hydroxypyrrolidin-3-ylcarbamate (2.020 g, 100%). 1 H NMR (400 MHz, MeOD) δ ppm 4.13 (dt, 1 H), 3.89-3.75 (m, 1 H), 3.35 (brs, 1 H), 3.14 (dd, 1 H), 2.93-2.73 (m, 2 H), 1.46 (s, 10 H); m/z 203.

Workup

  1. customwas degassed
  2. customThe mixture was degassed
  3. additioncharged with H2
  4. filtrationThe mixture was filtered through a bed of Celite
  5. washwashed with methanol
  6. dry with materialthe filtrate was dried over anhydrous Na2SO4
  7. filtrationfiltered and conc. in vacuo

Sources & evidence

ORD record
ord-753faf00c6974d0890a2e6003146e0ee
Source dataset
uspto-grants-2014_12
Patent number
US08901307B2

Reaction notes

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