1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68913725, compound

HRID 732647Notes

Reaction equation

HRID 732647 reaction equation
C([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)[C@@H:10]([CH2:20][O:21][Si](C(C)(C)C)(C)C)[CH2:9]1)C1C=CC=CC=1.[C:29]([O:38][CH2:39][CH3:40])(=[O:37])[CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O-:36])=O.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>ClCCl>[F:19][C:15]1[CH:14]=[C:13]([C@@H:11]2[C@@H:10]([CH2:20][OH:21])[CH2:9][N:8]([C:34](=[O:36])[CH2:33][CH2:32][CH2:31][CH2:30][C:29]([O:38][CH2:39][CH3:40])=[O:37])[CH2:12]2)[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 6993579HCID 6993579, compoundHCID 68913625HCID 68913625, compound

Product 1

HCID 68913725HCID 68913725, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 240 mg portion of [(3R,4S)-4-(3-fluorophenyl)pyrrolidin-3-yl]methanol obtained by eliminating benzyl from (3R,4S)-1-benzyl-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(3-fluorophenyl)pyrrolidine in the same manner as in Reference Example 17 was dissolved in 2.4 ml of dichloromethane, mixed with 235 mg of monoethyl adipate, 229 mg of WSC and 199 mg of HOBt and stirred at room temperature for 3Hours. The reaction solution was washed with water and dried with anhydrous sodium sulfate, and then the solvent was evaporated under a reduced pressure. By purifying the residue by a silica gel column chromatography (chloroform-methanol), 320 mg of ethyl 6-[(3S,4R)-3-(3-fluorophenyl)-4-(hydroxymethyl)pyrrolidin-1-yl]-6-oxohexanoate was obtained as a pale yellow oily substance.

Workup

  1. washThe reaction solution was washed with water
  2. dry with materialdried with anhydrous sodium sulfate
  3. customthe solvent was evaporated under a reduced pressure
  4. customBy purifying the residue by a silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-4fca8f334e354927834d1064223002be
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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