2-Morpholinoethanol → HCID 131729101, compound

HRID 1671435Notes

Reaction equation

HRID 1671435 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:26])([CH3:25])[CH:11]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[C:12]([OH:14])=[O:13])(=[O:7])=[O:6].C(Cl)(=O)C(Cl)=O.[N:33]1([CH2:39][CH2:40]O)[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>ClCCl>[Cl:1][CH2:2][CH2:3][CH2:4][S:5]([O:8][CH2:9][C:10]([CH3:26])([CH3:25])[CH:11]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[C:12]([O:14][CH2:40][CH2:39][N:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1)=[O:13])(=[O:7])=[O:6]

Participants

5

Reactant 3

HCID 611632-MorpholinoethanolHCID 65578Oxalyl chlorideHCID 87601326HCID 87601326, compound

Product 1

HCID 131729101HCID 131729101, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Following the general procedure for the preparation of carboxylic esters from carboxylic acids of Description 15, (2R/S)-4-[(3-chloropropyl)sulfonyloxy]-2-[(4-methoxyphenyl)methoxy]-3,3-dimethylbutanoic acid (14) (0.5 g, 1.2 mmol) dissolved in 5 mL of anhydrous dichloromethane (DCM) was reacted with 0.14 mL (0.2 g, 0.14 mmol) of oxalyl chloride. After completion of the reaction, a solution of 0.37 g (2.8 mmol) of 2-morpholin-4-yl ethanol in anhydrous dichloromethane (DCM) was added to the acid chloride. After work-up, the crude material was purified by silica gel column chromatography using ethyl acetate as eluent to provide 0.22 g (35% yield) of the title compound (27a) as a colorless oil. Rf=0.67 (EtOAc). 1H NMR (400 MHz, CDCl3): δ=1.07 (s, 3H), 1.09 (s, 3H), 2.26-2.32 (m, 2H), 2.53-2.70 (m, 6H), 3.22-3.26 (m, 2H), 3.65-3.69 (m, 6H), 3.82 (s, 3H), 3.84 (s, 1H), 4.02 (d, J=9.2 Hz, 1H), 4.19 (d, J=8.8 Hz, 1H), 4.30-4.38 (m, 3H), 4.59 (d, J=9.2 Hz, 1H), 6.88 (d, J=7.2 Hz, 2H), 7.27 (d, J=6.8 Hz, 2H) ppm. MS (ESI) m/z 529.09 (M+H)+.

Workup

  1. customAfter completion of the reaction
  2. customAfter work-up, the crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-60559809efeb42848c762de97beec3d3
Source dataset
uspto-grants-2011_08
Patent number
US07994218B2

Reaction notes

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