Ethyl 5-methylhex-2-ynoate → HCID 25070151, compound

HRID 237871Notes

Reaction equation

HRID 237871 reaction equation
[CH:1]12[CH:9]([C:10]3[CH:23]=[CH:22][C:13]([O:14][CH2:15][C@H:16]4[O:20][C:19]([NH2:21])=[N:18][CH2:17]4)=[CH:12][CH:11]=3)[CH:5]([CH2:6][CH2:7][CH2:8]1)[CH2:4][CH2:3][CH2:2]2.C([O:26][C:27](=O)[C:28]#[C:29][CH2:30][CH:31]([CH3:33])[CH3:32])C>C(O)C>[CH:1]12[CH:9]([C:10]3[CH:23]=[CH:22][C:13]([O:14][CH2:15][C@H:16]4[O:20][C:19]5=[N:21][C:27](=[O:26])[CH:28]=[C:29]([CH2:30][CH:31]([CH3:33])[CH3:32])[N:18]5[CH2:17]4)=[CH:12][CH:11]=3)[CH:5]([CH2:4][CH2:3][CH2:2]1)[CH2:6][CH2:7][CH2:8]2

Participants

4

Reactant 2

HCID 12383857Ethyl 5-methylhex-2-ynoateHCID 68527534(S)-5-(4-bicyclo[3.3.1]non-9-yl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine

Product 1

HCID 25070151HCID 25070151, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of (S)-5-(4-bicyclo[3.3.1]non-9-yl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine (0.600 g, 1.91 mmol) in ethanol (5 mL) was added 0.294 g (2.86 mmol) of 5-methyl-hex-2-ynoic acid ethyl ester. The reaction mixture was heated in a microwave oven at 160° C. for 20 minutes. The reaction mixture was concentrated and purified by chromatography on silica gel eluting with MeOH/CH2Cl2 to afford 0.283 g of the title compound. [α]D25 −11.17 (c 0.537, CHCl3).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by chromatography on silica gel eluting with MeOH/CH2Cl2

Sources & evidence

ORD record
ord-60a06bbd5187403cbb87bca7e585e68e
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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