Ethanol → HCID 22986047, compound

HRID 1263620Notes

Reaction equation

HRID 1263620 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][C@H:8]1[CH:20]=O)=[O:6])[CH:2]=[CH2:3].C(O)C.[C:25]1([NH2:35])[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1.C([BH3-])#N.[Na+]>C(O)(=O)C>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:9][C@H:8]1[CH2:20][NH:35][C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1)=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 702EthanolHCID 86401-NaphthylamineHCID 5003444Sodium cyanoborohydrideHCID 10892428HCID 10892428, compound

Product 1

HCID 22986047HCID 22986047, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of (2S,4S)-2-formyl4-BOCsulfanyl-pyrrolidine-1-carboxylic acid allyl ester (compound(1)) ( 711 mg), ethanol(25 ml), 1-naphthylamine(333 mg) and 3A molecular sieves(4.5 g.) was stirred under an argon atmosphere at ambient temperature for 6 hours. Acetic acid (0.4 ml) was added followed by sodium cyanoborohydride(l 70 mg). The mixture was then stirred for a further 20 hours when the sieves were removed by filtration. The filtrate was concentrated under reduced pressure and the residue applied to a silica column and eluted with ethyl acetate/hexane(20:80) to give (2S,4S)-1-allyloxycarbonyl-2[(naphthalen-1-ylamino )-methyl]-4-BOCsulfanylpyrrolidine (compound(31)) as a clear oil (560 mg).

Workup

  1. stirringThe mixture was then stirred for a further 20 hours when the sieves
  2. customwere removed by filtration
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. washeluted with ethyl acetate/hexane(20:80)

Sources & evidence

ORD record
ord-e4df715f320c48699ff06e7f3d3fba1d
Source dataset
uspto-grants-2003_04
Patent number
US06541491B1

Reaction notes

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