tert-Butanol → HCID 68089406, compound

HRID 1918227Notes

Reaction equation

HRID 1918227 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C:10]([CH3:23])(C(O)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[N:26]([CH:30](C)C)C(C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:40])C=CC=CC=1.[C:50]([OH:54])([CH3:53])([CH3:52])[CH3:51]>>[C:50]([O:54][C:30](=[O:40])[NH:26][C@:10]1([CH3:23])[C@@H:11]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[CH2:12][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9]1)([CH3:53])([CH3:52])[CH3:51]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 68089260HCID 68089260, compound

Product 1

HCID 68089406HCID 68089406, compound

Procedure

A mixture of 5.6 g (17 mmol) rac-(3R,4R)-1-Benzyl-4-(4-chloro-phenyl)-3-methyl-pyrrolidine-3-carboxylic acid, 2.4 g (18.7 mmol) DIPEA and 5.14 g (18.7 mmol) diphenylphosphoryl azide in 120 mL tert.-butanol was heated to reflux over night. The mixture was concentrated under vacuum and purified by column chromatography on silica eluting with a gradient formed from heptane and ethyl acetate to yield after evaporation of the product containing fractions 4.63 g (68%) of the title compound as yellow viscous oil. MS m/e: 401.3 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux over night
  3. concentrationThe mixture was concentrated under vacuum
  4. custompurified by column chromatography on silica eluting with a gradient
  5. customformed from heptane and ethyl acetate
  6. customto yield
  7. customafter evaporation of the product
  8. additioncontaining fractions 4.63 g (68%) of the title compound as yellow viscous oil

Sources & evidence

ORD record
ord-1446ea946d1e4acf861854d6a212830a
Source dataset
uspto-grants-2013_12
Patent number
US08618303B2

Reaction notes

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