2-Methyl-2-butanol → 931409-24-4

HRID 2382577Notes

Reaction equation

HRID 2382577 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[O:5][CH:6]1[CH2:9][N:8]([C:10]([CH3:29])([CH3:28])[CH2:11][CH2:12][C:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:14]#[N:15])[CH2:7]1.C([OH:38])(CC)(C)C.[OH-].[K+]>>[OH:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[O:5][CH:6]1[CH2:9][N:8]([C:10]([CH3:29])([CH3:28])[CH2:11][CH2:12][C:13]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:14]([NH2:15])=[O:38])[CH2:7]1

Participants

4

Reactant 3

HCID 64052-Methyl-2-butanolHCID 14797Potassium HydroxideHCID 59423887HCID 59423887, compound

Product 1

HCID 16065403931409-24-4

Conditions

Temperature
80 °C

Procedure

A suspension of 5-[3-(3-Hydroxyphenoxy)azetidin-1-yl]-5-methyl-2,2-diphenyl-hexanenitrile (0.16 g, 0.38 mmol, 1 equiv), t-amyl alcohol (1.8 ml, 12 ml/g) and KOH (0.41 g, 7.26 mmol, 20 equiv) was heated to 80° C. for 2 d whereupon HPLC showed completion of reaction. The reaction was cooled to ambient then partitioned between water and TBME, the aqueous layer was acidified to pH 8 with aq HCl, layers separated and the organic layer concentrated to afford 5-[3-(3-Hydroxyphenoxy)azetidin-1-yl]-5-methyl-2,2-diphenylhexanamide as a colourless oil, 0.11 g (68%).

Workup

  1. customcompletion of reaction
  2. temperatureThe reaction was cooled
  3. customto ambient then partitioned between water and TBME
  4. customseparated
  5. concentrationthe organic layer concentrated

Sources & evidence

ORD record
ord-31bcf7f1d03e49a88a73795b3da74287
Source dataset
uspto-grants-2012_09
Patent number
US08263583B2

Reaction notes

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