Acetyl chloride → Methyl 3-acetyltricyclo[3.3.1.03,7]nonane-1-carboxylate

HRID 1015506Notes

Reaction equation

HRID 1015506 reaction equation
[C:1]([C:4]12[CH2:11][CH:10]3[CH2:12][C:6]([C:13]([OH:15])=[O:14])([CH2:7][CH:8]1[CH2:9]3)[CH2:5]2)(=[O:3])[CH3:2].[C:16](Cl)(=O)C>CO>[C:1]([C:4]12[CH2:11][CH:10]3[CH2:12][C:6]([C:13]([O:15][CH3:16])=[O:14])([CH2:7][CH:8]1[CH2:9]3)[CH2:5]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 593749503-Acetyltricyclo[3.3.1.03,7]nonane-1-carboxylic acid

Product 1

HCID 67017872Methyl 3-acetyltricyclo[3.3.1.03,7]nonane-1-carboxylateYield 94.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 3-acetyltricyclo[3.3.1.03,7]nonane-1-carboxylic acid (2.4 g, 11.4 mmol) obtained in step I, in MeOH (48 mL) cooled to ice bath temperature, was added acetyl chloride (1.64 mL, 22.8 mmol). The reaction mixture was gradually warmed to room temperature and stirred for 2 h. The volatiles were removed under reduced pressure and the crude product was purified by column chromatography to obtain methyl 3-acetyltricyclo[3.3.1.03,7]nonane-1-carboxylate (2.4 g) in 93% yield as viscous liquid. m/z (M+1) 223. IR cm−1 2953, 1728, 1698, 1461, 1234, 1078, 755. 1H NMR (CDCl3) 300 MHz δ 3.66 (s, 3H), 2.75-2.70 (m, 1H), 2.53-2.46 (m, 1H), 2.40-2.32 (m, 1H), 2.19 (s, 3H), 2.15-2.05 (m, 1H), 2.03-1.60 (m, 8H). 13C NMR (CDCl3) 75 MHz δ 210.9, 175.3, 61.4, 53.4, 51.6, 50.5, 48.0, 45.9, 45.6, 42.6, 41.9, 36.8, 35.9, 26.4.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-605c889d938246c6b715e3d4e5ae5057
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

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