Diisopropylethylamine → HCID 67661897, compound

HRID 1599161Notes

Reaction equation

HRID 1599161 reaction equation
C(N(C(C)C)CC)(C)C.[C:10]1([C@H:16]([CH3:20])[C:17](O)=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl.CN(C)CCCN=C=NCC.[C:33]([CH2:35][C@@H:36]1[CH2:44][C@@H:43]2[C@@H:39]([CH2:40][NH:41][CH2:42]2)[C@@:38]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=2[O:52][CH3:53])([OH:45])[CH2:37]1)#[N:34]>ClCCl.O.OC1C2N=NNC=2C=CC=1>[C:33]([CH2:35][C@@H:36]1[CH2:44][C@@H:43]2[C@@H:39]([CH2:40][N:41]([C:17](=[O:18])[C@H:16]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH3:20])[CH2:42]2)[C@@:38]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=2[O:52][CH3:53])([OH:45])[CH2:37]1)#[N:34]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27246222-Phenylpropionic acid, (+)-HCID 53899359HCID 53899359, compound

Product 1

HCID 67661897HCID 67661897, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 178526939HCID 178526939, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

0.87 cm3 of diisopropylethylamine, 0.75 g of (S)-2-phenylpropionic acid, 0.02 g of hydroxybenzotriazole hydrate and 1.05 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride are added to a solution of 1.43 g of (3aS,4S,6S,7aR)-6-cyanomethyl-4-(2-methoxyphenyl)perhydroisoindol-4-ol in 20 cm3 of dichloromethane. The reaction mixture is stirred at 20° C. for 20 hours and then washed twice with 30 cm3 of water, dried over magnesium sulphate and then concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is chromatographed on a silica gel column (particle size 0.04-0.063 mm, height 32 cm, diameter 2.8 cm), eluting under a pressure of 0.6 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (50:50 by volume) and collecting fractions of 25 cm3. Fractions 19 to 35 are concentrated to dryness under reduced pressure (2.7 kPa). 1.20 g of (3aS,4S,6S,7aR)-6-cyanomethyl-4-(2-methoxyphenyl)-2-[(S)-2-phenylpropionyl]perhydroisoindol-4-ol in the form of a thick white foam are obtained.

Workup

  1. washwashed twice with 30 cm3 of water
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customThe residue obtained
  5. customis chromatographed on a silica gel column (particle size 0.04-0.063 mm, height 32 cm, diameter 2.8 cm)
  6. washeluting under a pressure of 0.6 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (50:50 by volume)
  7. customcollecting fractions of 25 cm3
  8. concentrationFractions 19 to 35 are concentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-ad7829d827e442d1842e154238c637ed
Source dataset
uspto-grants-1998_04
Patent number
US05739351

Reaction notes

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