Ethyl Acetate → HCID 19926551, compound

HRID 1647212Notes

Reaction equation

HRID 1647212 reaction equation
[CH2:1]([N:4]([C@@H:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][C:23]=2[OH:27])[CH2:18]1)[CH2:5][CH2:6][C@H:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=O)[O:8]1)[CH2:2][CH3:3].CCOC(C)=O>C1COCC1>[CH:7]1([CH2:6][CH2:5][N:4]([CH2:1][CH2:2][CH3:3])[CH:17]2[CH2:26][CH2:25][C:24]3[C:23]([OH:27])=[CH:22][CH:21]=[CH:20][C:19]=3[CH2:18]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][O:8]1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 18655859HCID 18655859, compound

Product 1

HCID 19926551HCID 19926551, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A racemic mixture of the product of Example 36 (66 mg, 0.180 mmol) was dissolved in THF and added dropwise to a solution of BH3 in THF (2 mL) and the mixture was refluxed overnight. After workup the crude mixture was subjected to flash chromatography (Silica: EtOAc) and the product showed characteristic peaks at: NMR (300 MHz, CDCl3) δ7.3-6.5(m, 7H), 5.4-5.0(m, 3H), 0.9(t, 3H). Anal. calc. for C22H29NO2 ° HCl: Theor. C; 71.21; H; 7.79; N, 3.61. Observed: C, 71.16, H, 7.61; N, 3.55.

Workup

  1. temperaturethe mixture was refluxed overnight

Sources & evidence

ORD record
ord-da2e477283aa414b8a0c3c197f6bb73d
Source dataset
uspto-grants-1995_07
Patent number
US05430056

Reaction notes

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