Triethylamine → phenylmethyl [((3R,4R)-4-hydroxy-1-{2-[7-(methyloxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]ethyl}-3-pyrrolidinyl)methyl]carbamate

HRID 657007

Reaction equation

HRID 657007 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:16])[N:10]2[CH2:13][CH:14]=O)=[N:5][CH:4]=1.[OH:17][C@H:18]1[CH2:22][NH:21][CH2:20][C@H:19]1[CH2:23][NH:24][C:25](=[O:34])[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(CC)CC)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO.C(Cl)(Cl)Cl>[OH:17][C@H:18]1[CH2:22][N:21]([CH2:14][CH2:13][N:10]2[C:11]3[C:6](=[N:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=3)[CH:7]=[CH:8][C:9]2=[O:16])[CH2:20][C@H:19]1[CH2:23][NH:24][C:25](=[O:34])[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 57815194(7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehydeHCID 86616784Phenylmethyl {[(3S,4R)-4-hydroxy-3-pyrrolidinyl]methyl}carbamate

Product 1

HCID 86635332phenylmethyl [((3R,4R)-4-hydroxy-1-{2-[7-(methyloxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]ethyl}-3-pyrrolidinyl)methyl]carbamateYield 73%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

To a solution of [7-(methoxy)-2-oxo-1,5-naphthyridin-1(2H)-yl]acetaldehyde (as the methyl hemiacetal) (0.500 g, 2.29 mmol) in 1:1 (MeOH/CHCl3) (40 mL) were added phenylmethyl {[(3S,4R)-4-hydroxypyrrolidin-3-yl]methyl}carbamate (0.658 g, 2.29 mmol) and triethylamine (0.351 mL, 2.52 mmol). The resulting solution was stirred at ambient temperature for 1 h. Na(OAc)3BH (1.46 g, 6.87 mmol) was added and the solution stirred at rt for an additional 18 h. The reaction mixture was concentrated onto silica gel and chromatographed on a silica gel column [0-100% CHCl3/(90:10:1) CHCl3/MeOH/NH4OH)] to yield a colorless oil (0.760 g, 73%).

Workup

  1. stirringthe solution stirred at rt for an additional 18 h
  2. concentrationThe reaction mixture was concentrated onto silica gel
  3. customchromatographed on a silica gel column [0-100% CHCl3/(90:10:1) CHCl3/MeOH/NH4OH)]

Sources & evidence

ORD record
ord-06c0363007eb4083869ac5dd9aad6f0c
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Linked notes

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