Morpholine → HCID 57609695, compound

HRID 416674Notes

Reaction equation

HRID 416674 reaction equation
C([O:4][C:5](=[O:35])[CH:6]([N:16]([C:26](=[O:34])[CH:27]([CH2:31][CH2:32][Cl:33])[C:28](=[O:30])[CH3:29])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[CH2:7][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)C=C.N1CCOCC1>C1COCC1.CCOCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:9]([O:8][CH2:7][CH:6]([N:16]([C:26](=[O:34])[CH:27]([CH2:31][CH2:32][Cl:33])[C:28](=[O:30])[CH3:29])[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1)[C:5]([OH:35])=[O:4])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 2

HCID 8083MorpholineHCID 75237320HCID 75237320, compound

Product 1

HCID 57609695HCID 57609695, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of allyl ester 76 (1.24 g, 2.47 mmol) in THF (20 mL) was added morpholine (646 mg, 7.41 mmol) and Pd(PPh3)4 (29 mg, 0.025 mmol) at ambient temperature. The reaction mixture was stirred at ambient temperature for 7 h and diluted with Et2O (200 mL). The organic layer was washed with 0.2 N HCl and brine, dried over MgSO4 and concentrated. The residue was purified by flash chromatography on SiO2 (15:85 acetone:CH3Cl) to give acid 77 (620 mg, 75%). Data provided for only one diastereomer: IR (neat) 1721, 1639 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.20-7.40 (m, 7H), 6.89 (d, J=8.7 Hz, 2H), 4.82 (d, J=16.5 Hz, 1H), 4.70 (d, J=16.5 Hz, 1H), 4.48 (s, 2H), 4.41-4.45 (m, 1H), 4.00-4.10 (m, 3H), 3.84 (s, 3H), 3.50-3.65 (m, 2H), 2.20-2.50 (m, 2H), 2.13 (s, 3H); LRMS (ESI) Calcd. for C24H28ClNO6 [M−H] 460, found 460.

Workup

  1. washThe organic layer was washed with 0.2 N HCl and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography on SiO2 (15:85 acetone:CH3Cl)

Sources & evidence

ORD record
ord-8469613ffa4f4cb79ac4d6dbbf1a921a
Source dataset
uspto-grants-2012_01
Patent number
US08088923B2

Reaction notes

Loading…