HCID 53986256, compound → HCID 22818939, compound

HRID 1106041Notes

Reaction equation

HRID 1106041 reaction equation
[C:1]([N:11]1[CH2:18][C:17](=[CH:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[H][H]>C(O)C.[Pt](=O)=O>[C:1]([N:11]1[CH2:18][C@@H:17]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

5

Reactant 2

HCID 53986256HCID 53986256, compoundHCID 178418361HCID 178418361, compound4×

Product 1

HCID 22818939HCID 22818939, compoundYield 87.9%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A solution of 5.3 g (0.014 mole) of N-carbobenzyloxy-4-[(4-chlorophenyl)methylene]-L-proline in 150 ml of ethanol is treated with 0.45 g of platinum dioxide and shaken on a Parr hydrogenator at a starting pressure of 15 lbs. (bottle gauge). The uptake of hydrogen is carefully monitored and whenever the pressure falls to 5 lbs the bottle is replenished with hydrogen to 15 lbs. A noticeable slowing down of the rate of hydrogen uptake is observed after eight minutes and the hydrogenation is interrupted after a total of ten minutes (21.5 lbs of hydrogen). The catalyst is filtered off (celite bed under nitrogen atmosphere), washed well with ethanol, and the combined filtrates are evaporated, finally at 0.2 mm, to yield 4.6 g of N-carbobenzyloxy-cis-4-[(4-chlorophenyl)methyl]-L-proline as a colorless brittle foam.

Workup

  1. filtrationThe catalyst is filtered off (celite bed under nitrogen atmosphere)
  2. washwashed well with ethanol
  3. customthe combined filtrates are evaporated, finally at 0.2 mm

Sources & evidence

ORD record
ord-f929c8893a884c16a0a075891b7d489d
Source dataset
uspto-grants-1982_01
Patent number
US04311705

Reaction notes

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