(4R)-4-benzyloxy-1-t-butoxycarbonyl-2-{2-[2-(3-methylphenyl)ethyl]phenoxymethyl}pyrrolidine → (4R)-1-t-butoxycarbonyl-4-hydroxy-2-{2-[2-(3-methylphenyl)ethyl]phenoxymethyl}pyrrolidine

HRID 743303Notes

Reaction equation

HRID 743303 reaction equation
C([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:11]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([CH3:37])[CH:32]=2)[CH2:10]1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[C:17]([O:16][C:14]([N:12]1[CH2:13][C@H:9]([OH:8])[CH2:10][CH:11]1[CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH3:37])[CH:32]=1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 2

HCID 54190298(4R)-4-benzyloxy-1-t-butoxycarbonyl-2-{2-[2-(3-methylphenyl)ethyl]phenoxymethyl}pyrrolidineHCID 178418361HCID 178418361, compound

Product 1

HCID 54479635(4R)-1-t-butoxycarbonyl-4-hydroxy-2-{2-[2-(3-methylphenyl)ethyl]phenoxymethyl}pyrrolidineYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Following a procedure similar to that described in Example 65(b), 550 mg of (4R)-4-benzyloxy-1-t-butoxycarbonyl-2-{2-[2-(3-methylphenyl)ethyl]phenoxymethyl}pyrrolidine [prepared as described in step (a) above] were dissolved in 20 ml of ethanol and hydrogenated in an atmosphere of hydrogen at atmospheric pressure and in the presence of 120 mg of 5% w/w palladium-on-charcoal as a catalyst. The mixture was then worked up as described in Example 65(b), and the crude product thus obtained was purified by column chromatography through silica gel, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 370 mg (yield 82%) of the title compound as a colorless oil.

Workup

  1. customthe crude product thus obtained
  2. customwas purified by column chromatography through silica gel
  3. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-0f841d0c9a064d928038748d6a15b8ce
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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