Ammonium Chloride → 9H-fluoren-9-ylmethyl (3S,5R)-3-hydroxymethyl-5-(3,4,5-trifluorophenyl)morpholine-4-carboxylate

HRID 553961Notes

Reaction equation

HRID 553961 reaction equation
Cl[C:2]([O:4][CH2:5][CH:6]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)=[O:3].[F:19][C:20]1[CH:21]=[C:22]([C@H:28]2[NH:33][C@@H:32]([CH2:34][OH:35])[CH2:31][O:30][CH2:29]2)[CH:23]=[C:24]([F:27])[C:25]=1[F:26].C(=O)(O)[O-].[Na+].[Cl-].[NH4+]>ClCCl>[OH:35][CH2:34][C@H:32]1[CH2:31][O:30][CH2:29][C@@H:28]([C:22]2[CH:21]=[C:20]([F:19])[C:25]([F:26])=[C:24]([F:27])[CH:23]=2)[N:33]1[C:2]([O:4][CH2:5][CH:6]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)=[O:3]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 343679-Fluorenylmethyl chloroformateHCID 516892Sodium BicarbonateHCID 67373759[(3S,5R)-5-(3,4,5-trifluorophenyl)morpholin-3-yl]methanol

Product 1

HCID 673732639H-fluoren-9-ylmethyl (3S,5R)-3-hydroxymethyl-5-(3,4,5-trifluorophenyl)morpholine-4-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

9-Fluorenylmethyl chloroformate (327 mg) was added to a mixed solution of [(3S,5R)-5-(3,4,5-trifluorophenyl)morpholin-3-yl]methanol (250 mg) in dichloromethane (5 mL) and a saturated sodium bicarbonate solution (5 mL), and the reaction solution was stirred at room temperature for six hours. Dichloromethane and a saturated ammonium chloride solution were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: heptane->heptane:ethyl acetate=2:1) to obtain 470 mg of the title compound. The property values of the compound are as follows.

Workup

  1. customthe organic layer was separated
  2. dry with materialThe resulting organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (elution solvent: heptane->heptane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-8bf7ad4ff91b48c19369939401fb287a
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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