1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-Isopropoxy-3-methylbenzaldehyde

HRID 1478444Notes

Reaction equation

HRID 1478444 reaction equation
C(O[C@H]1C[C@@H](C2C=CN=CC=2)OC2(CCNCC2)C1)C.CCN=C=NCCCN(C)C.[CH:32]([O:35][C:36]1[CH:44]=[CH:43][C:39]([C:40](O)=[O:41])=[CH:38][C:37]=1[CH3:45])([CH3:34])[CH3:33].CCN(C(C)C)C(C)C>ClCCl>[CH:32]([O:35][C:36]1[CH:44]=[CH:43][C:39]([CH:40]=[O:41])=[CH:38][C:37]=1[CH3:45])([CH3:34])[CH3:33]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 592729354-Isopropoxy-3-methylbenzoic acidHCID 117772903cis-8-Ethoxy-10-(4-pyridyl)-11-oxa-3-azaspiro[5.5]undecane

Product 1

HCID 509982434-Isopropoxy-3-methylbenzaldehydeYield 146.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of cis-8-ethoxy-10-(4-pyridyl)-11-oxa-3-azaspiro[5.5]undecane (50 mg, 0.18 mmol), EDCI (38 mg, 0.20 mmol) and 4-isopropoxy-3-methyl-benzoic acid (35 mg, 0.18 mmol) in dichloromethane (0.9 mL) was treated with DIPEA (94 μL, 0.54 mmol) and stirred for 16 h. The reaction mixture was filtered and purified by reverse phase HPLC (1-100% ACN/water) to afford cis-8-ethoxy-10-(2-pyridyl)-11-oxa-3-azaspiro[5.5]undecan-3-yl)(4-isopropoxy-3-methyl-phenyl)methanone (47 mg, 57.58%). ESI-MS m/z calc. 452.27, found 453.2 (M+1)+; Retention time: 1.059 minutes (3 min run).

Workup

  1. filtrationThe reaction mixture was filtered
  2. custompurified by reverse phase HPLC (1-100% ACN/water)

Sources & evidence

ORD record
ord-756a9414e76e4a0d9abc053532773dd7
Source dataset
uspto-grants-2016_08
Patent number
US09403839B2

Reaction notes

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