Phenylmethyl[(3s)-3-pyrrolidinylmethyl]carbamate → phenylmethyl[((3S)-1-{(2S)-2-hydroxy-2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]carbamate

HRID 639075Notes

Reaction equation

HRID 639075 reaction equation
[C:1]1([CH2:7][O:8][C:9](=[O:17])[NH:10][CH2:11][C@H:12]2[CH2:16][CH2:15][NH:14][CH2:13]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][O:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[C:23]([C@H:30]3[CH2:32][O:31]3)[CH:24]=[CH:25][N:26]=2)[N:21]=1>CN(C=O)C>[C:1]1([CH2:7][O:8][C:9](=[O:17])[NH:10][CH2:11][C@@H:12]2[CH2:16][CH2:15][N:14]([CH2:32][C@@H:30]([OH:31])[C:23]3[C:22]4[C:27](=[CH:28][CH:29]=[C:20]([O:19][CH3:18])[N:21]=4)[N:26]=[CH:25][CH:24]=3)[CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 45072662Phenylmethyl[(3s)-3-pyrrolidinylmethyl]carbamateHCID 592543592-(methyloxy)-8-[(2S)-2-oxiranyl]-1,5-naphthyridine

Product 1

HCID 59026170phenylmethyl[((3S)-1-{(2S)-2-hydroxy-2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]carbamateYield 25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of phenylmethyl[(3S)-3-pyrrolidinylmethyl]carbamate (0.53 g, 2.27 mmole) and LiClO4 (0.24 g, 2.27 mmole) in DMF (1 mL) was added 2-(methyloxy)-8-[(2S)-2-oxiranyl]-1,5-naphthyridine (0.45 g, 2.25 mmole). After 24 h at 80° C., the reaction contents were purified on silica gel (CHCl3/MeOH, 9:1, containing 5% NH4OH) to afford the title compound (0.24 g, 25%) as a light yellow oil: LC-MS (ES) m/e 437 (M+H)+.

Workup

  1. customthe reaction contents
  2. customwere purified on silica gel (CHCl3/MeOH, 9:1, containing 5% NH4OH)

Sources & evidence

ORD record
ord-1805254b459c413584df967b8b8c4a76
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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