HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium borohydride → Methyl (3r,4r)-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]-4-[3-(r,s)-amino-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate

HRID 393216
Notes
Print preview

Reaction equation

HRID 393216 reaction equation
[BH4-].[Na+].[F:3][C:4]1[C:9]([F:10])=[CH:8][C:7]([F:11])=[CH:6][C:5]=1[C:12]#[C:13][CH2:14][N:15]1[CH2:20][CH2:19][C@@H:18]([CH2:21][CH2:22][C:23](=[N:36]O)[C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[C:31]([O:34][CH3:35])[CH:32]=3)[N:27]=[CH:26][CH:25]=2)[C@@H:17]([C:38]([O:40][CH3:41])=[O:39])[CH2:16]1>CO.[Mo]=O>[F:3][C:4]1[C:9]([F:10])=[CH:8][C:7]([F:11])=[CH:6][C:5]=1[C:12]#[C:13][CH2:14][N:15]1[CH2:20][CH2:19][C@@H:18]([CH2:21][CH2:22][CH:23]([NH2:36])[C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[C:31]([O:34][CH3:35])[CH:32]=3)[N:27]=[CH:26][CH:25]=2)[C@@H:17]([C:38]([O:40][CH3:41])=[O:39])[CH2:16]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 136380444methyl (3R,4R)-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]-4-[3-hydroxyimino-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate

Product 1

HCID 131724622Methyl (3r,4r)-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]-4-[3-(r,s)-amino-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylateYield 45.1%

Reagents, catalysts & solvents 2

HCID 139765
Molybdenum oxide
Catalyst
HCID 887MethanolSolvent

Procedure

1.44 g of sodium borohydride and 0.77 g of molybdenum oxide are added with stirring and under an inert atmosphere, at a temperature in the region of −5° C., to a solution of 2.05 g of methyl (3R,4R)-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]-4-[3-hydroxyimino-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate in 100 cm3 of methanol. After 5 hours at a temperature in the region of 20° C., the mixture is concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. The residue is purified by chromatography at atmospheric pressure on a column of silica gel (particle size 20-45μ; mass 30 g), elution being carried out with a dichloromethane/methanol/triethylamine (89/10/1 by volume) mixture. Fractions 3 to 5 (containing the purified product) are combined and then concentrated to dryness under the above conditions. 0.9 g of methyl (3R,4R)-1-[3-(2,3,5-trifluorophenyl)prop-2-ynyl]-4-[3-(R,S)-amino-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate is obtained.

Workup

  1. concentrationthe mixture is concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C
  2. customThe residue is purified by chromatography at atmospheric pressure on a column of silica gel (particle size 20-45μ; mass 30 g), elution
  3. additionFractions 3 to 5 (containing the purified product)
  4. concentrationconcentrated to dryness under the above conditions

Sources & evidence

ORD record
ord-83d7dfc587c34a479d72ffac7d9dc5b1
Source dataset
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06806277B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes