tert-Butanol → HCID 68089163, compound

HRID 1918233Notes

Reaction equation

HRID 1918233 reaction equation
[CH2:1]([N:8]1[CH2:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)([CH3:13])[CH:10](C(O)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1.CC[N:43]([CH:47](C)C)C(C)C.[C:50]([OH:54])([CH3:53])([CH3:52])[CH3:51]>>[C:50]([O:54][C:47](=[O:31])[NH:43][C@H:10]1[C@@:11]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)([CH3:13])[CH2:12][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9]1)([CH3:53])([CH3:52])[CH3:51]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 68089279HCID 68089279, compound

Product 1

HCID 68089163HCID 68089163, compound

Procedure

A mixture of 4.9 g (14 9 mmol) rac-(3S,4R)-1-Benzyl-4-(4-chloro-phenyl)-4-methyl-pyrrolidine-3-carboxylic acid, 4.5 g (16.3 mmol) diphenylphosphoryl azide and 2.1 g (16.3 mmol) DIPEA in 80 mL tert.-butanol was heated to reflux over night. The mixture was concentrated, taken up on isolute and subjected to purification by chromatography on silica eluting with a gradient formed from heptane and ethyl acetate to yield after evaporation of the product containing fractions 3.8 g (64%) of the title compound as light yellow viscous oil. MS m/e: 401.4 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux over night
  3. concentrationThe mixture was concentrated
  4. customsubjected to purification by 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 3.8 g (64%) of the title compound as light yellow viscous oil

Sources & evidence

ORD record
ord-c253e707040b45d198bacf7c2d4ce5c5
Source dataset
uspto-grants-2013_12
Patent number
US08618303B2

Reaction notes

Loading…