Acetic Anhydride → HCID 18396011, compound

HRID 1075549Notes

Reaction equation

HRID 1075549 reaction equation
[C:1]([O:5][C@H:6]1[CH2:15][CH2:14][CH2:13][C@@H:12]2[C@:7]1([CH3:17])[CH2:8][CH2:9][CH2:10][C@@H:11]2[OH:16])([CH3:4])([CH3:3])[CH3:2].[C:18](OC(=O)C)(=[O:20])[CH3:19]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:1]([O:5][C@H:6]1[CH2:15][CH2:14][CH2:13][C@@H:12]2[C@:7]1([CH3:17])[CH2:8][CH2:9][CH2:10][C@@H:11]2[O:16][C:18](=[O:20])[CH3:19])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 21309361HCID 21309361, compound

Product 1

HCID 18396011HCID 18396011, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of 4.11 g (17.1 mMol) of (1S,4aS,5S,8aR)-5-tert-Butoxy-4a-methyl-decahydro-naphtalen-1-ol and 313.6 mg (2.6 mMol) of 4-dimethylaminopyridine in 26 ml of pyridine is treated with 13 ml of acetic anhydride under stirring and argon atmosphere for two hours. The reaction mixture is poured on ice-water and extracted three times with diethylether. The combined organic layer is washed twice with water, dried over sodium sulfate and evaporated in vacuo to yield 1.26 g of crude product which is chromatographed over 60 g of silicagel with hexane/ethylacetate 9/1 to give 4.64 g (91%) of Acetic acid (1S,4aS,5S,8aR)-5-tert-butoxy-4a-methyl-decahydronaphtalen -1-yl ester as an amorphous pure product.

Workup

  1. additionThe reaction mixture is poured on ice-water
  2. extractionextracted three times with diethylether
  3. washThe combined organic layer is washed twice with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customto yield 1.26 g of crude product which
  7. customis chromatographed over 60 g of silicagel with hexane/ethylacetate 9/1

Sources & evidence

ORD record
ord-adc7e29edba64730bf29f740ca174b1b
Source dataset
uspto-grants-1999_05
Patent number
US05905074

Reaction notes

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