Hydrochloric Acid → HCID 15172765, compound

HRID 2387758Notes

Reaction equation

HRID 2387758 reaction equation
[C:1]1([CH2:7][C@H:8]([OH:12])[C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.Cl>ClCCl>[OH:12][C@@H:8]([CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:9]([N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 4447183-Phenyllactic acid, (S)-HCID 2724699PyBOP

Product 1

HCID 15172765HCID 15172765, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A sample of (S)-3-phenyllactic acid (1, 21 g, 126 mmol) is dissolved in dichloromethane (300 mL) and treated with morpholine (55 g, 631 mmol). The reaction is cooled in an ice/water bath and a solution of PyBOP (72 g, 139 mmol) in dichloromethane (200 mL) is added dropwise through a pressure equalizing funnel. The reaction mixture is stirred overnight and allowed to warm to room temperature. After addition of 110 mL of 4 M HCl, the reaction mixture is filtered and the organics are separated. The aqueous layer is extracted twice with dichloromethane and discarded. The combined organics are dried over MgSO4 and the solvent is removed. The resulting material is chromatographed on silica gel and eluted with ethyl acetate to afford 20.65 g (68% yield) of (S)-2-hydroxy-1-morpholin-4-yl-3-phenyl-propan-1-one (2) as an oil; HPLC-MS calculated for C13H17NO3 (M+H+) 236.1, found 236.4.

Workup

  1. temperatureThe reaction is cooled in an ice/water bath
  2. filtrationthe reaction mixture is filtered
  3. customthe organics are separated
  4. extractionThe aqueous layer is extracted twice with dichloromethane
  5. dry with materialThe combined organics are dried over MgSO4
  6. customthe solvent is removed
  7. customThe resulting material is chromatographed on silica gel
  8. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-fe5d2e9513a34700916d1b72b9b3524c
Source dataset
uspto-grants-2012_09
Patent number
US08268996B2

Reaction notes

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