Ammonium Chloride → ethyl (2E)-3-(6-{(tert-butoxycarbonyl)[(3R)-1-(2-fluorobenzyl)-3-pyrrolidinyl]amino}-3-pyridyl)acrylate

HRID 2376029Notes

Reaction equation

HRID 2376029 reaction equation
Cl.Cl.[C:3]([O:7][C:8]([N:10]([C@@H:24]1[CH2:28][CH2:27][NH:26][CH2:25]1)[C:11]1[N:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][CH:12]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].C(N([CH:35]([CH3:37])[CH3:36])CC)(C)C.[F:38][C:39]1C=C(C=[CH:45][CH:46]=1)C=O.[C:47](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH4+].[Cl-]>ClCCCl>[C:3]([O:7][C:8]([N:10]([C@@H:24]1[CH2:28][CH2:27][N:26]([CH2:47][C:36]2[CH:35]=[CH:37][CH:45]=[CH:46][C:39]=2[F:38])[CH2:25]1)[C:11]1[N:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][CH:12]=1)=[O:9])([CH3:4])([CH3:5])[CH3:6]

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 680093-FluorobenzaldehydeHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86603639ethyl (2E)-3-(6-{(tert-butoxycarbonyl)[(3R)-3-pyrrolidinyl]amino}-3-pyridyl)acrylate dihydrochloride

Product 1

HCID 86603655ethyl (2E)-3-(6-{(tert-butoxycarbonyl)[(3R)-1-(2-fluorobenzyl)-3-pyrrolidinyl]amino}-3-pyridyl)acrylate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of ethyl (2E)-3-(6-{(tert-butoxycarbonyl)[(3R)-3-pyrrolidinyl]amino}-3-pyridyl)acrylate dihydrochloride (3.0 g) in 1,2-dichloroethane (30 mL) was added diisopropylethylamine (2.41 mL) and 3-fluorobenzaldehyde (857 mg), and the mixture was stirred at room temperature for 5 minutes. To the mixture was added sodium triacetoxyborohydride (3.1 g) and stirred for 3 hours, and resulting mixture was poured into sat NH4Cl aq solution, and extracted with AcOEt. The organic layer was washed with sat NH4Cl aq solution, water, and brine, and dried over Na2SO4. The solvent was removed in vacuo and the residual oil was purified by silica gel column chromatography eluted with AcOEt and hexane (1:1) to give ethyl (2E)-3-(6-{(tert-butoxycarbonyl)[(3R)-1-(2-fluorobenzyl)-3-pyrrolidinyl]amino}-3-pyridyl)acrylate (2.40 g) as colorless oil.

Workup

  1. stirringstirred for 3 hours
  2. customresulting mixture
  3. additionwas poured
  4. extractionextracted with AcOEt
  5. washThe organic layer was washed with sat NH4Cl aq solution, water, and brine
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed in vacuo
  8. customthe residual oil was purified by silica gel column chromatography
  9. washeluted with AcOEt and hexane (1:1)

Sources & evidence

ORD record
ord-bac1a6e41ee14ce2ad29f43d680c914b
Source dataset
uspto-grants-2008_12
Patent number
US07465731B2

Reaction notes

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