Benzyl Alcohol → HCID 131735706, compound

HRID 2200378Notes

Reaction equation

HRID 2200378 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.N1C=CC=CC=1.[CH3:30][C:31]1([CH3:44])[CH2:43][O:42][C:34]2([CH2:38][C@@H:37]([C:39](O)=[O:40])[CH2:36][CH2:35]2)[O:33][CH2:32]1>ClCCl.CC(C)=O>[CH3:30][C:31]1([CH3:44])[CH2:32][O:33][C:34]2([CH2:38][C@@H:37]([C:39]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:40])[CH2:36][CH2:35]2)[O:42][CH2:43]1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 58894626HCID 58894626, compound

Product 1

HCID 131735706HCID 131735706, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
27.5 °C

Procedure

Benzyl alcohol (7.28 ml, 70.0 mmol), DCC (0.43 g, 2.1 mmol) and a catalytic amount of 4-dimethylammino pyridine (0.20 g, 1.68 mmol) were successively added to a solution of (S)-8,8-dimethyl-6,10-dioxaspiro[4.5]decane-2-carboxylic acid (Synthesized following procedure as described in DE4312832 and US20080161564, 3 g, 14.00 mmol) in anhydrous Dichloromethane (50 ml). The reaction mixture was stirred for 24 h at 25-30° C. and then acetone (10 ml) was added. The resulting suspension was filtered and subsequently concentrated under vacuum. The residue was purified by silica gel column chromatography using ethyl acetate in hexane as eluents to obtain (S)-benzyl 8,8-dimethyl-6,10-dioxaspiro[4.5]decane-2-carboxylate (3.5 g, 82%).

Workup

  1. filtrationThe resulting suspension was filtered
  2. concentrationsubsequently concentrated under vacuum
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6c47d4b88fe243a9a92fd544b0d6a63b
Source dataset
uspto-grants-2016_06
Patent number
US09359367B2

Reaction notes

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